Co-reporter:Mu-Wang Chen, Yue Ji, Jie Wang, Qing-An Chen, Lei Shi, and Yong-Gui Zhou
Organic Letters September 15, 2017 Volume 19(Issue 18) pp:
Publication Date(Web):September 7, 2017
DOI:10.1021/acs.orglett.7b02502
By employing halogenide trichloroisocyanuric acid as a traceless activation reagent, a general iridium-catalyzed asymmetric hydrogenation of isoquinolines and pyridines is developed with up to 99% ee. This method avoids tedious steps of installation and removal of the activating groups. The mechanism studies indicated that hydrogen halide generated in situ acted as an activator of isoquinolines and pyridines.
Co-reporter:Ji Zhou;Mao-Lin Wang;Xiang Gao;Guo-Fang Jiang
Chemical Communications 2017 vol. 53(Issue 25) pp:3531-3534
Publication Date(Web):2017/03/23
DOI:10.1039/C7CC01072A
A bifunctional squaramide-catalyzed reaction of azlactones with o-quinone methides in situ generated from 2-(1-tosylalkyl)-phenols has been successfully developed under basic conditions, providing an efficient and mild access to chiral dihydrocoumarins bearing adjacent tertiary and quaternary stereogenic centers in high yields with excellent diastereo- and enantioselectivities.
Co-reporter:Bo Song;Chang-Bin Yu;Yue Ji;Mu-Wang Chen
Chemical Communications 2017 vol. 53(Issue 10) pp:1704-1707
Publication Date(Web):2017/01/31
DOI:10.1039/C6CC09493G
A novel palladium-catalyzed intramolecular reductive amination of ketones with weakly nucleophilic sulfonamides has been developed in the presence of a Brønsted acid, giving a wide range of chiral γ-, δ-, and ε-sultams in high yields and up to 99% of enantioselectivity.
Co-reporter:Yue Ji;Guang-Shou Feng;Mu-Wang Chen;Lei Shi;Haifeng Du
Organic Chemistry Frontiers 2017 vol. 4(Issue 6) pp:1125-1129
Publication Date(Web):2017/05/31
DOI:10.1039/C7QO00060J
An enantioselective hydrogenation of cyclic iminium salts has been successfully realized by employing [Ir(COD)Cl]2 and chiral diphosphine ligands as catalyst, furnishing chiral N-alkyl tetrahydroisoquinolines and N-alkyl tetrahydro-β-carbolines with up to 96% ee and 88% ee, respectively. The hydrogenation provides a direct, simple and efficient protocol toward chiral tertiary amines. Meanwhile, asymmetric hydrogenation at the gram scale was also conducted smoothly without loss of reactivity and enantioselectivity.
Co-reporter:Bo Song, Yue Ji, Shu-Bo Hu, Chang-Bin Yu, Yong-Gui Zhou
Tetrahedron Letters 2017 Volume 58, Issue 15(Issue 15) pp:
Publication Date(Web):12 April 2017
DOI:10.1016/j.tetlet.2017.03.012
•Synthesis of chiral γ-sultams through intramolecular reductive amination.•This tandem process avoids deprotection manipulation and isolation of the N-sulfonylimines.•Chiral palladium catalyst was well-compatible to moist, water and acidic condition.An efficient and enantioselective palladium-catalyzed intramolecular asymmetric reductive amination with sulfonylcarbamates as N-sources was reported, providing a facile and general access to the chiral γ-sultam derivatives with up to 97% of enantioselectivity. This tandem process avoids additional deprotection manipulation and arduous isolation of the N-sulfonyl-imine intermediates.Download high-res image (42KB)Download full-size image
Co-reporter:Shu-Bo Hu;Zhang-Pei Chen;Bo Song;Jie Wang
Advanced Synthesis & Catalysis 2017 Volume 359(Issue 16) pp:2762-2767
Publication Date(Web):2017/08/17
DOI:10.1002/adsc.201700431
AbstractAn enantioselective iridium-catalyzed direct hydrogenation of heteroaromatics containing two nitrogen atoms, 3-substituted pyrrolo[1,2-a]pyrazines, has been successfully achieved, providing a facile synthesis of optically active 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines with up to 96% ee.
Co-reporter:Jie Wang, Mu-Wang Chen, Yue Ji, Shu-Bo Hu, and Yong-Gui Zhou
Journal of the American Chemical Society 2016 Volume 138(Issue 33) pp:10413-10416
Publication Date(Web):August 12, 2016
DOI:10.1021/jacs.6b06009
An efficient kinetic resolution of axially chiral 5- or 8-substituted quinoline derivatives was developed through asymmetric transfer hydrogenation of heteroaromatic moiety, simultaneously obtaining two kinds of axially chiral skeletons with up to 209 of selectivity factor. This represents the first successful application of asymmetric transfer hydrogenation of heteroaromatics in kinetic resolution of axially chiral biaryls.
Co-reporter:Wen-Xue Huang, Chang-Bin Yu, Yue Ji, Lian-Jin Liu, and Yong-Gui Zhou
ACS Catalysis 2016 Volume 6(Issue 4) pp:2368
Publication Date(Web):March 3, 2016
DOI:10.1021/acscatal.5b02625
A highly enantioselective hydrogenation of heteroaromatics bearing a hydroxyl group, 3-hydroxypyridinium salts, has been successfully developed using chiral iridium catalyst, providing a direct access to trans 6-substituted piperidin-3-ols with up to 95% ee. Swern oxidation of the hydrogenation products affords chiral 6-substituted piperidin-3-ones, which are easily reduced to cis 6-substituted piperidin-3-ols using K-selectride.Keywords: 3-hydroxypyridinium salts; asymmetric hydrogenation; iridium; piperidin-3-ol; piperidin-3-one
Co-reporter:Hong-Qiang Shen, Xiang Gao, Cong Liu, Shu-Bo Hu, and Yong-Gui Zhou
Organic Letters 2016 Volume 18(Issue 22) pp:5920-5923
Publication Date(Web):November 4, 2016
DOI:10.1021/acs.orglett.6b03027
An iridium-catalyzed asymmetric hydrogenation/oxidative fragmentation of 6-substituted 5H-benzo[d] benzofuro[3,2-b]azepines has been developed, providing an efficient access to optically active 4-substituted 4,5-dihydro-1H-benzo[d]azepin-1-ones with up to 91% ee. A possible reaction pathway includes the asymmetric hydrogenation to furnish chiral cyclic amines and oxidative fragmentation under an air atmosphere.
Co-reporter:Mu-Wang Chen, Bo Wu, Zhang-Pei Chen, Lei Shi, and Yong-Gui Zhou
Organic Letters 2016 Volume 18(Issue 18) pp:4650-4653
Publication Date(Web):August 29, 2016
DOI:10.1021/acs.orglett.6b02283
A highly enantioselective synthesis of chiral fluorinated propargylamines was developed through phosphoric acid and ruthenium-catalyzed chemoselective biomimetic hydrogenation of the carbon–nitrogen double bond of fluorinated alkynyl ketimines in the presence of a carbon–carbon triple bond. This reaction features high chemoselectivity and slow background reaction. In addition, selective transformations of the chiral fluorinated propargylamines were also reported.
Co-reporter:Zhong Yan, Bo Wu, Xiang Gao, Mu-Wang Chen, and Yong-Gui Zhou
Organic Letters 2016 Volume 18(Issue 4) pp:692-695
Publication Date(Web):February 1, 2016
DOI:10.1021/acs.orglett.5b03664
A highly enantioselective palladium-catalyzed hydrogenation of a series of linear and cyclic α-iminophosphonates has been achieved, providing efficient access to optically active α-aminophosphonates with up to 99% ee.
Co-reporter:Zhang-Pei Chen, Shu-Bo Hu, Mu-Wang Chen, and Yong-Gui Zhou
Organic Letters 2016 Volume 18(Issue 11) pp:2676-2679
Publication Date(Web):May 19, 2016
DOI:10.1021/acs.orglett.6b01118
An enantioselective hydrogenation of fluorinated hydrazones has been achieved by employing [Pd(R)-DTBM-SegPhos(OCOCF3)2] as the catalyst, providing a general and convenient method toward chiral fluorinated hydrazines. A broad substrate scope including β-aryl-, γ-aryl-, and alkyl-chain-substituted hydrazones worked efficiently in high yields and up to 94% of enantioselectivity. The reductive amination between trifluoromethyl-substituted ketones and benzohydrazides could also proceed smoothly.
Co-reporter:Wen-Xue Huang, Lian-Jin Liu, Bo Wu, Guang-Shou Feng, Baomin Wang, and Yong-Gui Zhou
Organic Letters 2016 Volume 18(Issue 13) pp:3082-3085
Publication Date(Web):June 13, 2016
DOI:10.1021/acs.orglett.6b01190
A facile method has been developed for the synthesis of chiral piperazines through Ir-catalyzed hydrogenation of pyrazines activated by alkyl halides, giving a wide range of chiral piperazines including 3-substituted as well as 2,3- and 3,5-disubstituted ones with up to 96% ee. The high enantioselectivity, easy scalability, and concise drug synthesis demonstrate the practical utility.
Co-reporter:Xiang Gao, Bo Wu, Zhong Yan and Yong-Gui Zhou
Organic & Biomolecular Chemistry 2016 vol. 14(Issue 1) pp:55-58
Publication Date(Web):2015/11/24
DOI:10.1039/C5OB02330K
With the aid of an axially chiral 2,2′-bipyridine ligand, we have successfully developed a palladium-catalyzed method for the enantioselective arylation of N-tosylarylimines, furnishing the chiral diarylmethamines with high yields and enantioselectivities under very mild conditions. An exogenous base was avoided and imine hydrolysis was inhibited in this transformation.
Co-reporter:Guang-Shou Feng, Yue Ji, Hui-Fang Liu, Lei Shi, Yong-Gui Zhou
Tetrahedron Letters 2016 Volume 57(Issue 7) pp:747-749
Publication Date(Web):17 February 2016
DOI:10.1016/j.tetlet.2016.01.008
An unusual solvent DMF-promoted dehydrogenation of 1-substituted 1,2,3,4-tetrahydroisoquinolines to synthesize cyclic imines is described. This environmentally friendly reaction features no requirement of any metal catalysts, oxidants, or hydrogen acceptors. A wide range of structurally varied 3,4-dihydroisoquinolines can be obtained with good yields and excellent chemoselectivities.
Co-reporter:Yue Ji; Lei Shi; Mu-Wang Chen; Guang-Shou Feng
Journal of the American Chemical Society 2015 Volume 137(Issue 33) pp:10496-10499
Publication Date(Web):August 14, 2015
DOI:10.1021/jacs.5b06659
A concise deracemization of racemic secondary and tertiary amines with a tetrahydroisoquinoline core has been successfully realized by orchestrating a redox process consisted of N-bromosuccinimide oxidation and iridum-catalyzed asymmetric hydrogenation. This compatible redox combination enables one-pot, single-operation deracemization to generate chiral 1-substituted 1,2,3,4-tetrahydroisoquinolines with up to 98% ee in 93% yield, offering a simple and scalable synthetic technique for chiral amines directly from racemic starting materials.
Co-reporter:Zhang-Pei Chen, Shu-Bo Hu, Ji Zhou, and Yong-Gui Zhou
ACS Catalysis 2015 Volume 5(Issue 10) pp:6086
Publication Date(Web):September 14, 2015
DOI:10.1021/acscatal.5b01641
An efficient approach toward the synthesis of cyclic and linear chiral trifluoromethyl substituted hydrazines was developed by Pd-catalyzed asymmetric hydrogenation of both N-acyl and N-aryl hydrazones in excellent yields and up to 97% ee. A successful reductive amination between trifluoromethyl substituted ketones and hydrazines was also achieved.Keywords: asymmetric hydrogenation; Brønsted acid; palladium; reductive amination; trifluoromethylated hydrazines
Co-reporter:Bo Song, Chang-Bin Yu, Wen-Xue Huang, Mu-Wang Chen, and Yong-Gui Zhou
Organic Letters 2015 Volume 17(Issue 2) pp:190-193
Publication Date(Web):January 5, 2015
DOI:10.1021/ol503118v
Highly enantioselective palladium-catalyzed formal hydrogenolysis of racemic N-sulfonyloxaziridines has been realized, providing a novel access to sultams with up to 99% ee. Preliminary mechanistic insights revealed that the reaction proceeded through a N–O bond cleavage, dehydration, and the sequential asymmetric hydrogenation.
Co-reporter:Wen-Xue Huang, Bo Wu, Xiang Gao, Mu-Wang Chen, Baomin Wang, and Yong-Gui Zhou
Organic Letters 2015 Volume 17(Issue 7) pp:1640-1643
Publication Date(Web):March 24, 2015
DOI:10.1021/acs.orglett.5b00276
The selective hydrogenation of 3-hydroxypyridinium salts has been achieved using a homogeneous iridium catalyst, providing a direct access to 2- and 4-substituted piperidin-3-one derivatives with high yields, which are important organic synthetic intermediates and the prevalent structural motifs in pharmaceutical agents. Mild reaction conditions, high chemoselectivity, and easy scalability make this reaction highly practical for the synthesis of piperidin-3-ones.
Co-reporter:Bo Wu, Xiang Gao, Zhong Yan, Mu-Wang Chen, and Yong-Gui Zhou
Organic Letters 2015 Volume 17(Issue 24) pp:6134-6137
Publication Date(Web):December 10, 2015
DOI:10.1021/acs.orglett.5b03148
A streamlined method for the enantioselective synthesis of 2-amino-4H-chromenes from readily available 2-alkyl-substituted phenols and active methylene compounds bearing a cyano group with up to 97% ee is presented. This reaction is a cascade procedure including manganese dioxide mediated C–H oxidation for the generation of o-quinone methides and bifunctional squaramide-catalyzed Michael addition/cyclization.
Co-reporter:Bo Wu, Xiang Gao, Mu-Wang Chen, Yong-Gui Zhou
Tetrahedron Letters 2015 Volume 56(Issue 9) pp:1135-1137
Publication Date(Web):25 February 2015
DOI:10.1016/j.tetlet.2015.01.078
A metal-free and concise method for the selective synthesis of primary amines directly from 2-(1-tosylalkyl)phenols with aqueous ammonia under mild conditions has been developed. In addition, primary amine could be conveniently converted to benzoxazinone in good yield.
Co-reporter:Bo Wu, Xiang Gao, Zhong Yan, Wen-Xue Huang, Yong-Gui Zhou
Tetrahedron Letters 2015 Volume 56(Issue 29) pp:4334-4338
Publication Date(Web):15 July 2015
DOI:10.1016/j.tetlet.2015.05.076
An efficient bifunctional squaramide-catalyzed Michael addition/cyclization reaction of o-quinone methides generated in situ from 2-(1-tosylalkyl)phenols with active methylene compounds bearing a cyano group has been realized to synthesize chiral 2-amino-4H-chromenes with excellent enantioselectivities and broad substrate scope.
Co-reporter:Xiang Gao;Bo Wu;Wen-Xue Huang;Mu-Wang Chen; Yong-Gui Zhou
Angewandte Chemie 2015 Volume 127( Issue 41) pp:12124-12128
Publication Date(Web):
DOI:10.1002/ange.201504483
Abstract
A palladium-catalyzed enantioselective CH functionalization of indoles was achieved with an axially chiral 2,2′-bipyridine ligand, thus providing the desired indol-3-acetate derivatives with up to 98 % ee. Moreover, the reaction protocol was also effective for asymmetric OH insertion reaction of phenols using α-aryl-α-diazoacetates. This represents the first successful application of bipyridine ligands with axial chirality in palladium-catalyzed carbene migratory insertion reactions.
Co-reporter:Dr. Lei Shi;Dr. Yong-Gui Zhou
ChemCatChem 2015 Volume 7( Issue 1) pp:54-56
Publication Date(Web):
DOI:10.1002/cctc.201402838
Co-reporter:Xiang Gao;Bo Wu;Wen-Xue Huang;Mu-Wang Chen; Yong-Gui Zhou
Angewandte Chemie International Edition 2015 Volume 54( Issue 41) pp:11956-11960
Publication Date(Web):
DOI:10.1002/anie.201504483
Abstract
A palladium-catalyzed enantioselective CH functionalization of indoles was achieved with an axially chiral 2,2′-bipyridine ligand, thus providing the desired indol-3-acetate derivatives with up to 98 % ee. Moreover, the reaction protocol was also effective for asymmetric OH insertion reaction of phenols using α-aryl-α-diazoacetates. This represents the first successful application of bipyridine ligands with axial chirality in palladium-catalyzed carbene migratory insertion reactions.
Co-reporter:Ying Duan ; Lu Li ; Mu-Wang Chen ; Chang-Bin Yu ; Hong-Jun Fan
Journal of the American Chemical Society 2014 Volume 136(Issue 21) pp:7688-7700
Publication Date(Web):April 30, 2014
DOI:10.1021/ja502020b
An efficient palladium-catalyzed asymmetric hydrogenation of a variety of unprotected indoles has been developed that gives up to 98% ee using a strong Brønsted acid as the activator. This methodology was applied in the facile synthesis of biologically active products containing a chiral indoline skeleton. The mechanism of Pd-catalyzed asymmetric hydrogenation was investigated as well. Isotope-labeling reactions and ESI-HRMS proved that an iminium salt formed by protonation of the C═C bond of indoles was the significant intermediate in this reaction. The important proposed active catalytic Pd–H species was observed with 1H NMR spectroscopy. It was found that proton exchange between the Pd–H active species and solvent trifluoroethanol (TFE) did not occur, although this proton exchange had been previously observed between metal hydrides and alcoholic solvents. Density functional theory calculations were also carried out to give further insight into the mechanism of Pd-catalyzed asymmetric hydrogenation of indoles. This combination of experimental and theoretical studies suggests that Pd-catalyzed hydrogenation goes through a stepwise outer-sphere and ionic hydrogenation mechanism. The activation of hydrogen gas is a heterolytic process assisted by trifluoroacetate of Pd complex via a six-membered-ring transition state. The reaction proceeds well in polar solvent TFE owing to its ability to stabilize the ionic intermediates in the Pd–H generation step. The strong Brønsted acid activator can remarkably decrease the energy barrier for both Pd–H generation and hydrogenation. The high enantioselectivity arises from a hydrogen-bonding interaction between N–H of the iminium salt and oxygen of the coordinated trifluoroacetate in the eight-membered-ring transition state for hydride transfer, while the active chiral Pd complex is a typical bifunctional catalyst, effecting both the hydrogenation and hydrogen-bonding interaction between the iminium salt and the coordinated trifluoroacetate of Pd complex. Notably, the Pd-catalyzed asymmetric hydrogenation is relatively tolerant to oxygen, acid, and water.
Co-reporter:Chang-Bin Yu ; Wen-Xue Huang ; Lei Shi ; Mu-Wang Chen ; Bo Wu
Journal of the American Chemical Society 2014 Volume 136(Issue 45) pp:15837-15840
Publication Date(Web):October 29, 2014
DOI:10.1021/ja5075745
An efficient palladium-catalyzed asymmetric hydrogenation via capture of an active intermediate generated in situ from acid-catalyzed aza-Pinacol rearrangement has been successfully developed, providing efficient access to chiral exocyclic amines with up to 98% ee. Three-, four-, and five-membered cyclic N-sulfonyl amino alcohols are viable substrates. This study opens a new window to the application of asymmetric hydrogenation.
Co-reporter:Zhang-Pei Chen, Mu-Wang Chen, Ran-Ning Guo, and Yong-Gui Zhou
Organic Letters 2014 Volume 16(Issue 5) pp:1406-1409
Publication Date(Web):February 26, 2014
DOI:10.1021/ol500176v
A series of tunable and regenerable biomimetic hydrogen sources, 4,5-dihydropyrrolo[1,2-a]quinoxalines, have been synthesized and applied in biomimetic asymmetric hydrogenation of 3-aryl-2H-benzo[b][1,4]oxazines and 1-alkyl-3-aryl-quinoxalin-2(1H)-ones, providing the chiral amines with up to 92% and 89% ee, respectively.
Co-reporter:Xian-Feng Cai, Wen-Xue Huang, Zhang-Pei Chen and Yong-Gui Zhou
Chemical Communications 2014 vol. 50(Issue 67) pp:9588-9590
Publication Date(Web):04 Jul 2014
DOI:10.1039/C4CC04386C
Homogeneous Pd-catalyzed asymmetric hydrogenation of 3-phthalimido substituted quinolines was successfully developed, providing facile access to chiral substituted tetrahydroquinolines bearing two contiguous stereogenic centers with up to 90% ee.
Co-reporter:Mu-Wang Chen, Xian-Feng Cai, Zhang-Pei Chen, Lei Shi and Yong-Gui Zhou
Chemical Communications 2014 vol. 50(Issue 83) pp:12526-12529
Publication Date(Web):29 Aug 2014
DOI:10.1039/C4CC06060A
An efficient and facile route to chiral tetrahydroquinolines with three contiguous stereogenic centers via a dynamic kinetic resolution process has been successfully developed by using chiral phosphoric acid as catalyst and Hantzsch ester as the hydrogen source with up to 89% ee.
Co-reporter:Jing Luo, Bo Wu, Mu-Wang Chen, Guo-Fang Jiang, and Yong-Gui Zhou
Organic Letters 2014 Volume 16(Issue 10) pp:2578-2581
Publication Date(Web):May 6, 2014
DOI:10.1021/ol500948r
A concise synthesis of spiro-cyclopropane compounds from indole derivatives and sulfur ylides has been developed via a dearomatization strategy. Moreover, the spiro-cyclopropane compounds could be conveniently transformed to rearomatized indole derivatives in the presence of acids.
Co-reporter:Xian-Feng Cai, Ran-Ning Guo, Guang-Shou Feng, Bo Wu, and Yong-Gui Zhou
Organic Letters 2014 Volume 16(Issue 10) pp:2680-2683
Publication Date(Web):April 25, 2014
DOI:10.1021/ol500954j
A chiral phosphoric acid catalyzed asymmetric transfer hydrogenation of aromatic amines, quinolin-3-amines, was successfully developed with up to 99% ee. To supplement our previous work on the Ir-catalyzed asymmetric hydrogenation of 2-alkyl substituted quinolin-3-amines, a number of 2-aryl substituted substrates were reduced to provide a series of valuable chiral exocyclic amines with high diastereo- and enantioselectivities.
Co-reporter:Wen-Xue Huang, Chang-Bin Yu, Lei Shi, and Yong-Gui Zhou
Organic Letters 2014 Volume 16(Issue 12) pp:3324-3327
Publication Date(Web):June 9, 2014
DOI:10.1021/ol5013313
Highly enantioselective iridium-catalyzed hydrogenation of pyrrolo[1,2-a]pyrazinium salts has been achieved, providing a direct access to chiral 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine derivatives with up to 95% ee. The key feature of the reaction is the addition of cesium carbonate, which increases the conversion and prohibits the racemization pathway of products.
Co-reporter:Bo Wu;Mu-Wang Chen;Zhi-Shi Ye;Chang-Bin Yu
Advanced Synthesis & Catalysis 2014 Volume 356( Issue 2-3) pp:383-387
Publication Date(Web):
DOI:10.1002/adsc.201300830
Co-reporter:Ran-Ning Guo;Xian-Feng Cai;Lei Shi;Zhang-Pei Chen; Yong-Gui Zhou
Chemistry - A European Journal 2014 Volume 20( Issue 27) pp:8343-8346
Publication Date(Web):
DOI:10.1002/chem.201402282
Abstract
An efficient and transition-metal-free approach was developed to access a series of fluorinated heteroaromatics in moderate to excellent yields. This one-pot procedure features a triple-relay transformation of rapid dearomatization, fluorination, and rearomatization processes, which represents a conceptually novel strategy of combining partial hydrogenation and electrophilic fluorination.
Co-reporter:Xian-Feng Cai;Ran-Ning Guo;Mu-Wang Chen;Lei Shi; Yong-Gui Zhou
Chemistry - A European Journal 2014 Volume 20( Issue 24) pp:7245-7248
Publication Date(Web):
DOI:10.1002/chem.201402592
Abstract
Asymmetric hydrogenation of aromatic quinolin-3-amines was successfully developed with up to 94 % enantiomeric excess (ee). Introduction of the phthaloyl moiety to the amino group is crucial to eliminate the inhibition effect caused by the substrate and product, to activate the aromatic ring, and to improve the diastereoselectivity. This new methodology provides direct and facile access to chiral exocyclic amines. Notably, this report is the first on the highly enantioselective hydrogenation of aromatic amines.
Co-reporter:Qing-An Chen, Zhi-Shi Ye, Ying Duan and Yong-Gui Zhou
Chemical Society Reviews 2013 vol. 42(Issue 2) pp:497-511
Publication Date(Web):09 Nov 2012
DOI:10.1039/C2CS35333D
The transition metal catalyzed asymmetric hydrogenation of unsaturated compounds arguably presents one of the most attractive methods for the synthesis of chiral compounds. Over the last few decades, Pd has gradually grown up as a new and popular metal catalyst in homogeneous asymmetric hydrogenation the same as traditional Ru, Rh and Ir catalysts. Much progress has been successfully achieved in the asymmetric reduction of imines, enamines, olefins, ketones and heteroarenes. It was also found that palladium catalyzed asymmetric hydrogenation could be used as a key step in tandem reactions to quickly synthesize chiral compounds. This tutorial review intends to offer an overview of recent progress in homogeneous palladium catalyzed asymmetric hydrogenation and should serve as an inspiration for further advances in this area.
Co-reporter:Ran-Ning Guo, Xian-Feng Cai, Lei Shi, Zhi-Shi Ye, Mu-Wang Chen and Yong-Gui Zhou
Chemical Communications 2013 vol. 49(Issue 76) pp:8537-8539
Publication Date(Web):22 Jul 2013
DOI:10.1039/C3CC45341C
An efficient iridium-catalyzed asymmetric hydrogenation of the fluorinated isoquinoline derivatives has been successfully developed for the synthesis of chiral fluorinated tetrahydroisoquinoline derivatives with up to 93% ee. This methodology features the use of a hydrochloride salt as well as a catalytic amount of halogenated hydantoin which were vital for the reactivity, enantioselectivity, and inhibition of the hydrodefluorination pathway.
Co-reporter:Mu-Wang Chen, Liang-Liang Cao, Zhi-Shi Ye, Guo-Fang Jiang and Yong-Gui Zhou
Chemical Communications 2013 vol. 49(Issue 16) pp:1660-1662
Publication Date(Web):08 Jan 2013
DOI:10.1039/C3CC37800D
A novel and efficient method for the generation of o-quinone methide intermediates was developed from the readily available 2-tosylalkylphenols under the mild basic conditions, and their reactions with sulfur ylides were investigated for the stereoselective synthesis of trans-2,3-dihydrobenzofurans.
Co-reporter:Ying Duan, Xiao-Yan Zhu, Jun-An Ma, Yong-Gui Zhou
Tetrahedron Letters 2013 Volume 54(Issue 46) pp:6161-6163
Publication Date(Web):13 November 2013
DOI:10.1016/j.tetlet.2013.08.078
A series of fluorinated quinazolinones were hydrogenated using the chiral Pd/bisphosphine complex as the catalyst, giving the corresponding fluorinated dihydroquinazolinones with up to 98% enantioselectivity.A series of fluorinated quinazolinones were hydrogenated using the chiral Pd/bisphosphine complex as the catalyst, giving the corresponding fluorinated dihydroquinazolinones with up to 98% enantioselectivity.
Co-reporter:Zhi-Shi Ye;Ran-Ning Guo;Xian-Feng Cai;Mu-Wang Chen;Lei Shi ; Yong-Gui Zhou
Angewandte Chemie International Edition 2013 Volume 52( Issue 13) pp:3685-3689
Publication Date(Web):
DOI:10.1002/anie.201208300
Co-reporter:Dr. Chang-Bin Yu ; Yong-Gui Zhou
Angewandte Chemie 2013 Volume 125( Issue 50) pp:13607-13610
Publication Date(Web):
DOI:10.1002/ange.201307036
Co-reporter:Xian-Feng Cai;Mu-Wang Chen;Zhi-Shi Ye;Ran-Ning Guo;Dr. Lei Shi; Yan-Qin Li; Yong-Gui Zhou
Chemistry – An Asian Journal 2013 Volume 8( Issue 7) pp:1381-1385
Publication Date(Web):
DOI:10.1002/asia.201300380
Co-reporter:Zhi-Shi Ye;Ran-Ning Guo;Xian-Feng Cai;Mu-Wang Chen;Lei Shi ; Yong-Gui Zhou
Angewandte Chemie 2013 Volume 125( Issue 13) pp:3773-3777
Publication Date(Web):
DOI:10.1002/ange.201208300
Co-reporter:Dr. Chang-Bin Yu ; Yong-Gui Zhou
Angewandte Chemie International Edition 2013 Volume 52( Issue 50) pp:13365-13368
Publication Date(Web):
DOI:10.1002/anie.201307036
Co-reporter:Duo-Sheng Wang, Qing-An Chen, Sheng-Mei Lu, and Yong-Gui Zhou
Chemical Reviews 2012 Volume 112(Issue 4) pp:2557
Publication Date(Web):November 18, 2011
DOI:10.1021/cr200328h
Co-reporter:Kai Gao, Bo Wu, Chang-Bin Yu, Qing-An Chen, Zhi-Shi Ye, and Yong-Gui Zhou
Organic Letters 2012 Volume 14(Issue 15) pp:3890-3893
Publication Date(Web):July 17, 2012
DOI:10.1021/ol301620z
Highly enantioselective Ir-catalyzed hydrogenation of seven-membered cyclic imines of benzodiazepinones and benzodiazepines was achieved with up to 96% ee. This method provides a direct access to synthesize a range of chiral cyclic amines existing in numerous important natural products and clinical drugs.
Co-reporter:Mu-Wang Chen, Qing-An Chen, Ying Duan, Zhi-Shi Ye and Yong-Gui Zhou
Chemical Communications 2012 vol. 48(Issue 11) pp:1698-1700
Publication Date(Web):06 Dec 2011
DOI:10.1039/C2CC16832D
Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones, was developed using chiral phosphoric acid as catalyst and a Hantzsch ester as the hydrogen source with up to 95% ee. The reaction process of this asymmetric transfer hydrogenation may occur directly through the acyliminium ion intermediate.
Co-reporter:Kai Gao;Chang-Bin Yu;Duo-Sheng Wang
Advanced Synthesis & Catalysis 2012 Volume 354( Issue 2-3) pp:483-488
Publication Date(Web):
DOI:10.1002/adsc.201100568
Abstract
The highly enantioselective hydrogenation of 3-aryl-2H-1,4-benzoxazines was achieved using the (cyclooctadiene)iridium chloride dimer/(S)-SegPhos/iodine {[Ir(COD)Cl]2/(S)-SegPhos/I2} system as catalyst with up to 92% ee. The 3-styryl-2H-1,4-benzoxazine derivatives were also hydrogenated by the iridium catalyst and Pd/C in two consecutive steps whereby 93–95% ee values were obtained.
Co-reporter:Ying Duan, Mu-Wang Chen, Qing-An Chen, Chang-Bin Yu and Yong-Gui Zhou
Organic & Biomolecular Chemistry 2012 vol. 10(Issue 6) pp:1235-1238
Publication Date(Web):17 Nov 2011
DOI:10.1039/C1OB06777J
A series of 2-substituted 3-(toluenesulfonamidoalkyl)indoles was synthesized by application of (EtO)2POH or iodine as the catalyst, and was hydrogenated using chiral Pd catalyst, giving the 2,3-disubstituted indolines with up to 97% ee.
Co-reporter:Chang-Bin Yu, Kai Gao, Qing-An Chen, Mu-Wang Chen, Yong-Gui Zhou
Tetrahedron Letters 2012 Volume 53(Issue 20) pp:2560-2563
Publication Date(Web):16 May 2012
DOI:10.1016/j.tetlet.2012.03.035
Asymmetric hydrogenation of tetrasubstituted olefins of cyclic β-(arylsulfonamido)acrylates produces the corresponding cyclic β-(arylsulfonamido)propionates using Pd(OCOCF3)2/diphosphine complexes as catalysts in the presence of TFA with up to 96% ee.Asymmetric hydrogenation of tetrasubstituted olefins of cyclic β-(arylsulfonamido)acrylates produces the corresponding cyclic β-(arylsulfonamido)propionates using Pd(OCOCF3)2/diphosphine complexes as catalysts in the presence of trifluoro-acetic acid with up to 96% ee.
Co-reporter:De-Yang Zhang, Chang-Bin Yu, Min-Can Wang, Kai Gao, Yong-Gui Zhou
Tetrahedron Letters 2012 Volume 53(Issue 20) pp:2556-2559
Publication Date(Web):16 May 2012
DOI:10.1016/j.tetlet.2012.03.036
A new electronically deficient atropisomeric diphosphine ligand (S)-CF3O-BiPhep was synthesized from 1-bromo-3-(trifluoromethoxy)benzene in high yield. The key steps included oxidative coupling with anhydrous ferric chloride and optical resolution by (+)-DMTA. The ligand afforded high performance for Ir-catalyzed asymmetric hydrogenation of quinolines with ee up to 92% and TON up to 25,000. It was also successfully applied to the Pd-catalyzed asymmetric hydrogenation of simple indoles with ee up to 87% and Rh-catalyzed asymmetric 1,4-addition of phenylboronic acid to 2-cyclohexenone with 97% ee.A new electronically deficient atropisomeric diphosphine ligand (S)-CF3O-BiPhep was synthesized from 1-bromo-3-(trifluoromethoxy)benzene in high yield. The key steps included oxidative coupling with anhydrous ferric chloride and optical resolution by (+)-DMTA. The ligand afforded high performance for Ir-catalyzed asymmetric hydrogenation of quinolines with ee up to 92% and TON up to 25,000. It was also successfully applied to the Pd-catalyzed asymmetric hydrogenation of simple indoles with ee up to 87% and Rh-catalyzed asymmetric 1,4-addition of phenylboronic acid to 2-cyclohexenone with 97% ee.
Co-reporter:Zhi-Shi Ye;Mu-Wang Chen;Qing-An Chen;Lei Shi;Ying Duan ; Yong-Gui Zhou
Angewandte Chemie International Edition 2012 Volume 51( Issue 40) pp:10181-10184
Publication Date(Web):
DOI:10.1002/anie.201205187
Co-reporter:Dr. Lei Shi;Zhi-Shi Ye;Liang-Liang Cao;Ran-Ning Guo;Yue Hu ; Yong-Gui Zhou
Angewandte Chemie International Edition 2012 Volume 51( Issue 33) pp:8286-8289
Publication Date(Web):
DOI:10.1002/anie.201203647
Co-reporter:Zhi-Shi Ye;Mu-Wang Chen;Qing-An Chen;Lei Shi;Ying Duan ; Yong-Gui Zhou
Angewandte Chemie 2012 Volume 124( Issue 40) pp:10328-10331
Publication Date(Web):
DOI:10.1002/ange.201205187
Co-reporter:Dr. Lei Shi;Zhi-Shi Ye;Liang-Liang Cao;Ran-Ning Guo;Yue Hu ; Yong-Gui Zhou
Angewandte Chemie 2012 Volume 124( Issue 33) pp:8411-8414
Publication Date(Web):
DOI:10.1002/ange.201203647
Co-reporter:Qing-An Chen ; Duo-Sheng Wang ; Yong-Gui Zhou ; Ying Duan ; Hong-Jun Fan ; Yan Yang ;Zhang Zhang
Journal of the American Chemical Society 2011 Volume 133(Issue 16) pp:6126-6129
Publication Date(Web):April 5, 2011
DOI:10.1021/ja200723n
A convergent asymmetric disproportionation of dihydroquinoxalines for the synthesis of chiral tetrahydroquinoxalines using a metal/Brønsted acid relay catalysis system has been developed. The use of hydrogen gas as the reductant makes the convergent disproportionation an ideal atom-economical process. A dramatic reversal of enantioselectivity was observed in the reduction of quinoxalines because of the different steric demands in the 1,2- and 1,4-hydride transfer pathways.
Co-reporter:Duo-Sheng Wang ; Zhi-Shi Ye ; Qing-An Chen ; Yong-Gui Zhou ; Chang-Bin Yu ; Hong-Jun Fan ;Ying Duan
Journal of the American Chemical Society 2011 Volume 133(Issue 23) pp:8866-8869
Publication Date(Web):May 17, 2011
DOI:10.1021/ja203190t
A highly enantioselective Pd-catalyzed partial hydrogenation of simple 2,5-disubstituted pyrroles with a Brønsted acid as an activator has been successfully developed, providing chiral 2,5-disubstituted 1-pyrrolines with up to 92% ee.
Co-reporter:Qing-An Chen ; Mu-Wang Chen ; Chang-Bin Yu ; Lei Shi ; Duo-Sheng Wang ; Yan Yang
Journal of the American Chemical Society 2011 Volume 133(Issue 41) pp:16432-16435
Publication Date(Web):September 20, 2011
DOI:10.1021/ja208073w
A catalytic amount of Hantzsch ester that could be regenerated in situ by Ru complexes under hydrogen gas has been employed in the biomimetic asymmetric hydrogenation of benzoxazinones with up to 99% ee in the presence of chiral phosphoric acid. The use of hydrogen gas as a reductant for the regeneration of Hantzsch esters makes this hydrogenation an ideal atom economic process.
Co-reporter:Duo-Sheng Wang, Jie Tang, Yong-Gui Zhou, Mu-Wang Chen, Chang-Bin Yu, Ying Duan and Guo-Fang Jiang
Chemical Science 2011 vol. 2(Issue 4) pp:803-806
Publication Date(Web):24 Jan 2011
DOI:10.1039/C0SC00614A
Highly enantioselective hydrogenation of 3-(α-hydroxyalkyl)indoles promoted by a Brønsted acid for dehydration to form a vinylogous iminium intermediate in situ was developed with Pd(OCOCF3)2/(R)-H8-BINAP as catalyst with up to 97% ee. This methodology provides an efficient and rapid access to chiral 2,3-disubstituted indolines.
Co-reporter:Kai Gao, Chang-Bin Yu, Wei Li, Yong-Gui Zhou and Xumu Zhang
Chemical Communications 2011 vol. 47(Issue 27) pp:7845-7847
Publication Date(Web):31 May 2011
DOI:10.1039/C1CC12263K
Highly enantioselective hydrogenation of seven-membered cyclic imines, substituted dibenzo[b,f][1,4]oxazepines, was achieved, with up to 94% ee, by using the [Ir(COD)Cl]2/(S)-Xyl-C3*-TunePhos complex as the catalyst in the presence of morpholine-HCl.
Co-reporter:Chang-Bin Yu, Kao Gao, Duo-Sheng Wang, Lei Shi and Yong-Gui Zhou
Chemical Communications 2011 vol. 47(Issue 17) pp:5052-5054
Publication Date(Web):24 Mar 2011
DOI:10.1039/C1CC10313J
Asymmetric hydrogenation of cyclic enesulfonamides affords chiral cyclic sulfonamides using Pd(OCOCF3)2/diphosphine complexes as catalysts with up to 98% ee.
Co-reporter:Liang-Liang Cao;Zhi-Shi Ye;Guo-Fang Jiang
Advanced Synthesis & Catalysis 2011 Volume 353( Issue 18) pp:3352-3356
Publication Date(Web):
DOI:10.1002/adsc.201100577
Abstract
The rhodium-catalyzed addition of arylboronic acids to vinylogous imines generated in situ from sulfonylindoles has been developed. This procedure provided a rapid approach to C-3 sec-alkyl-substituted indoles.
Co-reporter:Xiao-Yu Zhou;Ming Bao
Advanced Synthesis & Catalysis 2011 Volume 353( Issue 1) pp:84-88
Publication Date(Web):
DOI:10.1002/adsc.201000554
Abstract
Using a catalytic amount of a Brønsted acid as activator of simple imines, the highly enantioselective homogeneous palladium-catalyzed asymmetric hydrogenation of simple ketimines was successfully developed with up to 95% ee.
Co-reporter:Liang-Liang Cao, Duo-Sheng Wang, Guo-Fang Jiang, Yong-Gui Zhou
Tetrahedron Letters 2011 Volume 52(Issue 22) pp:2837-2839
Publication Date(Web):1 June 2011
DOI:10.1016/j.tetlet.2011.03.099
An efficient route to 2,3-disubstituted indoles was developed via reductive alkylation of 2-substituted indoles using hydrogen as a clean and atom economic reductant under ambient pressure.An efficient route to 2,3-disubstituted indoles was developed via reductive alkylation of 2-substituted indoles using hydrogen as a clean and atom economic reductant under ambient pressure.
Co-reporter:Xiao-Yu Zhou, Duo-Sheng Wang, Ming Bao, Yong-Gui Zhou
Tetrahedron Letters 2011 Volume 52(Issue 22) pp:2826-2829
Publication Date(Web):1 June 2011
DOI:10.1016/j.tetlet.2011.03.057
Homogeneous Pd(OCOCF3)2/(R)-C4-TunePhos has been successfully applied in the asymmetric hydrogenation of simple ketones activated by catalytic amount of Brønsted acid with up to 88% ee.Homogeneous Pd(OCOCF3)2/(R)-C4-TunePhos has been successfully applied in the asymmetric hydrogenation of unfunctionalized ketones activated by catalytic amount of Brønsted acid with up to 88% ee.
Co-reporter:Ying Duan;Mu-Wang Chen;Zhi-Shi Ye;Duo-Sheng Wang;Qing-An Chen ; Yong-Gui Zhou
Chemistry - A European Journal 2011 Volume 17( Issue 26) pp:7193-7197
Publication Date(Web):
DOI:10.1002/chem.201100576
Co-reporter:Duo-Sheng Wang ; Qing-An Chen ; Wei Li ; Chang-Bin Yu ; Yong-Gui Zhou ;Xumu Zhang
Journal of the American Chemical Society 2010 Volume 132(Issue 26) pp:8909-8911
Publication Date(Web):June 16, 2010
DOI:10.1021/ja103668q
The first highly enantioselective hydrogenation of simple indoles was developed with a Brønsted acid as an activator to form the iminium intermediate in situ, which was hydrogenated using Pd(OCOCF3)2/(R)-H8-BINAP catalyst system with up to 96% ee. The present method provides an efficient route to enantioenriched 2-substituted and 2,3-disubstituted indolines.
Co-reporter:Qing-An Chen, Xiang Dong, Mu-Wang Chen, Duo-Sheng Wang, Yong-Gui Zhou and Yu-Xue Li
Organic Letters 2010 Volume 12(Issue 9) pp:1928-1931
Publication Date(Web):April 13, 2010
DOI:10.1021/ol100536e
A series of axially chiral bis-sulfoxide ligands have been efficiently synthesized via oxidative coupling with high diastereoselectivities. The axial chirality is well controlled by the tert-butylsulfinyl or the p-tolylsulfinyl group. These axially chiral bis-sulfoxides proved to be remarkably efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to 2-cyclohexenone with 99% ee.
Co-reporter:Qing-An Chen, Duo-Sheng Wang and Yong-Gui Zhou
Chemical Communications 2010 vol. 46(Issue 23) pp:4043-4051
Publication Date(Web):11 May 2010
DOI:10.1039/C001089H
The discovery and progress of new bifunctional AgOAc-based catalysts for asymmetric reactions is described. In this bifunctional procedure, AgOAc acts as an efficient Lewis acid catalyst as well as a base through the deprotonation of active hydrogen promoted by acetate. The bifunctional strategy offers a great opportunity to establish new fundamentals for stereoselective construction of C–C as well as C–N bonds.
Co-reporter:Mu-Wang Chen, Ying Duan, Qing-An Chen, Duo-Sheng Wang, Chang-Bin Yu, and Yong-Gui Zhou
Organic Letters 2010 Volume 12(Issue 21) pp:5075-5077
Publication Date(Web):October 4, 2010
DOI:10.1021/ol1020256
An enantioselective hydrogenation of simple fluorinated imines has been developed using Pd(OCOCF3)2/(R)-Cl-MeO-BIPHEP as a catalyst, and up to 94% ee was achieved. This method provides an efficient route to enantioenriched fluorinated amines.
Co-reporter:Duo-Sheng Wang, Yong-Gui Zhou
Tetrahedron Letters 2010 Volume 51(Issue 22) pp:3014-3017
Publication Date(Web):2 June 2010
DOI:10.1016/j.tetlet.2010.04.004
Enantioselective hydrogenation of quinolines and quinoxalines catalyzed by iridium/diphosphine complex with catalytic amount of Brønsted acid as activator was developed. In the presence of piperidine·TfOH as the activator, full conversions and up to 92% ee were obtained.Enantioselective hydrogenation of quinolines and quinoxalines catalyzed by iridium/diphosphine complex with catalytic amount of Brønsted acid as activator was developed. In the presence of piperidine·TfOH as the activator, full conversions and up to 92% ee were obtained.
Co-reporter:Duo-Sheng Wang, Juan Zhou, Da-Wei Wang, Yin-Long Guo, Yong-Gui Zhou
Tetrahedron Letters 2010 Volume 51(Issue 3) pp:525-528
Publication Date(Web):20 January 2010
DOI:10.1016/j.tetlet.2009.11.075
Introducing bulky groups on the coordination phosphorus atoms can effectively block the formation of inactive dimer species and improve the activity of the iridium catalysts. Results of ESI-MS analysis gave strong evidence. This strategy was successfully applied to the asymmetric hydrogenation of quinolines with up to 93% ee on S/C ratio of 25,000.Introducing bulky groups on the coordination phosphorus atoms can effectively block the formation of inactive species and improve the activity of the iridium catalysts. Results of ESI-MS analysis gave strong evidence. This strategy was successfully applied to the asymmetric hydrogenation of quinolines with up to 93% ee on S/C ratio of 25,000.
Co-reporter:Da-Wei Wang Dr.;Duo-Sheng Wang;Qing-An Chen
Chemistry - A European Journal 2010 Volume 16( Issue 4) pp:1133-1136
Publication Date(Web):
DOI:10.1002/chem.200902790
Co-reporter:Long-Wu Ye, Shou-Bing Wang, Qing-Gang Wang, Xiu-Li Sun, Yong Tang and Yong-Gui Zhou
Chemical Communications 2009 (Issue 21) pp:3092-3094
Publication Date(Web):15 Apr 2009
DOI:10.1039/B900048H
The reaction of a crotonate-derived chiral phosphonium salt with α,β-unsaturated carbonyl compounds in the presence of Cs2CO3 affords optically active cyclohexa-1,3-diene derivatives with up to 90% ee in good yields.
Co-reporter:Xiao-Bing Wang, Da-Wei Wang, Sheng-Mei Lu, Chang-Bin Yu, Yong-Gui Zhou
Tetrahedron: Asymmetry 2009 Volume 20(Issue 9) pp:1040-1045
Publication Date(Web):21 May 2009
DOI:10.1016/j.tetasy.2009.03.037
Co-reporter:Qing-An Chen, Wei Zeng, Yong-Gui Zhou
Tetrahedron Letters 2009 50(49) pp: 6866-6868
Publication Date(Web):
DOI:10.1016/j.tetlet.2009.09.124
Co-reporter:Da-Wei Wang, Xiao-Bing Wang, Duo-Sheng Wang, Sheng-Mei Lu, Yong-Gui Zhou and Yu-Xue Li
The Journal of Organic Chemistry 2009 Volume 74(Issue 7) pp:2780-2787
Publication Date(Web):March 9, 2009
DOI:10.1021/jo900073z
The enantioselective hydrogenation of 2-benzylquinolines and 2-functionalized and 2,3-disubstituted quinolines was developed by using the [Ir(COD)Cl]2/bisphosphine/I2 system with up to 96% ee. Moreover, mechanistic studies revealed the hydrogenation mechanism of quinoline involves a 1,4-hydride addition, isomerization, and 1,2-hydride addition, and the catalytic active species may be a Ir(III) complex with chloride and iodide.
Co-reporter:Da-Wei Wang, Sheng-Mei Lu, Yong-Gui Zhou
Tetrahedron Letters 2009 50(12) pp: 1282-1285
Publication Date(Web):
DOI:10.1016/j.tetlet.2008.12.108
Co-reporter:Yong-Gui Zhou
Accounts of Chemical Research 2007 Volume 40(Issue 12) pp:1357
Publication Date(Web):September 27, 2007
DOI:10.1021/ar700094b
Asymmetric hydrogenation of heteroaromatic compounds has emerged as a promising new route to saturated or partially saturated chiral heterocyclic compounds. In this Account, we outline recent advances in asymmetric hydrogenation of heteroaromatic compounds, including indole, quinoline, isoquinoline, furan, and pyridine derivatives, using chiral organometallic catalysts and organocatalysts.
Co-reporter:Da-Wei Wang, Wei Zeng, Yong-Gui Zhou
Tetrahedron: Asymmetry 2007 Volume 18(Issue 9) pp:1103-1107
Publication Date(Web):29 May 2007
DOI:10.1016/j.tetasy.2007.04.028
The iridium-catalyzed enantioselective transfer hydrogenation of quinolines with Hantzsch esters was developed with up to 88% ee using [Ir(COD)Cl]2/(S)-SegPhos/I2 as a catalyst.(S)-2-Methyl-1,2,3,4-tetrahydroquinolineC10H13N[α]D = −73.2 (c 0.56, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)(S)-2-Ethyl-1,2,3,4-tetrahydroquinolineC11H15N[α]D = −70.9 (c 0.66, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)(S)-2-Butyl-1,2,3,4-tetrahydroquinolineC13H19N[α]D = −72.2 (c 0.92, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)(S)-2-Pentyl-1,2,3,4-tetrahydroquinolineC14H21N[α]D = −41.3 (c 0.92, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)(S)-6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinolineC10H12FN[α]D = −54.4 (c 0.70, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)(S)-2,6-Dimethyl-1,2,3,4-tetrahydroquinolineC11H15N[α]D = −65.3 (c 0.62, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)(S)-6-Methoxy-2-methyl-1,2,3,4-tetrahydroquinolineC11H15NO[α]D = −63.5 (c 0.36, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)(S)-2-Phenethyl-1,2,3,4-tetrahydroquinolineC17H19N[α]D = −67.2 (c 1.14, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)(S)-2-(3′,4′-Methylenedioxyphenethyl)-1,2,3,4-tetrahydroquinolineC18H19NO2[α]D = −50.0 (c 1.19, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)(S)-2-(3′,4′-Dimethoxyphenethyl)-1,2,3,4-tetrahydroquinolineC19H23NO2[α]D = −43.8 (c 1.34, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)(R)-1,1-Diphenyl-2-(1,2,3,4-tetrahydroquinolin-2-yl)-ethanolC23H23NO[α]D = −82.6 (c 1.18, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)(R)-2-Phenyl-1,2,3,4-tetrahydroquinolineC15H15N[α]D = +7.6 (c 0.88, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)
Co-reporter:Sheng-Mei Lu Dr.;You-Qing Wang Dr.;Xiu-Wen Han
Angewandte Chemie 2006 Volume 118(Issue 14) pp:
Publication Date(Web):3 MAR 2006
DOI:10.1002/ange.200503073
Aktiver Bestandteil: Optisch aktive Tetrahydrochinoline und Tetrahydroisochinoline lassen sich durch asymmetrische Hydrierung von Chinolinen bzw. Isochinolinen mit Chlorformiaten wie ClCO2Bn als aktivierenden Reagentien herstellen (siehe Schema). Auf diese Art gelang die asymmetrische Synthese vieler natürlicher Alkaloide. Bn=Benzyl.
Co-reporter:Sheng-Mei Lu, You-Qing Wang, Xiu-Wen Han,Yong-Gui Zhou
Angewandte Chemie International Edition 2006 45(14) pp:2260-2263
Publication Date(Web):
DOI:10.1002/anie.200503073
Co-reporter:Sheng-Mei Lu;Xiu-Wen Han
Advanced Synthesis & Catalysis 2004 Volume 346(Issue 8) pp:
Publication Date(Web):5 AUG 2004
DOI:10.1002/adsc.200404017
Chiral ferrocenyloxazoline derived N,P ligands are used in the iridium-catalyzed asymmetric hydrogenation of quinolines, and up to 92% ee was obtained. The role of the planar chirality is also studied.
Co-reporter:Peng-Yu Yang, Yong-Gui Zhou
Tetrahedron: Asymmetry 2004 Volume 15(Issue 7) pp:1145-1149
Publication Date(Web):5 April 2004
DOI:10.1016/j.tetasy.2004.02.012
The first total synthesis of (−)-galipeine was accomplished in seven steps with 54% overall yield from isovanillin based on Ir-catalyzed asymmetric hydrogenation of a quinoline derivative as a key step, with its absolute stereochemistry being established.Graphic(−)-(S)-2-(3′-Benzyloxy-4′-methoxy-phenethyl)-1,2,3,4-tetrahydroquinolineC25H27NO2Ee=96% (by chiral HPLC)[α]20D=−38.6 (c 1.0, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: S(−)-(S)-2-(3′-Benzyloxy-4′-methoxy-phenethyl)-2,3,4-tetrahydro-1-methylquinolineC26H29NO2Ee=96%[α]20D=−16.1 (c 0.8, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: S(−)-(S)-2-(3′-Hydroxy-4′-methoxy-phenethyl)-2,3,4-tetrahydro-1-methylquinolineC19H23NO2Ee=96% (by chiral HPLC)[α]20D=−26.1 (c 0.44, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: S
Co-reporter:Xiang Gao, Bo Wu, Zhong Yan and Yong-Gui Zhou
Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 35) pp:NaN8240-8240
Publication Date(Web):2016/08/04
DOI:10.1039/C6OB01516F
Using copper complexes with an axially chiral bipyridine ligand C4-ACBP as the catalyst, an enantioselective functionalization of indoles with diazo compounds was developed with up to 95% ee. This protocol paves the way for further applications of these ligands.
Co-reporter:Bo Song, Chang-Bin Yu, Yue Ji, Mu-Wang Chen and Yong-Gui Zhou
Chemical Communications 2017 - vol. 53(Issue 10) pp:NaN1707-1707
Publication Date(Web):2017/01/05
DOI:10.1039/C6CC09493G
A novel palladium-catalyzed intramolecular reductive amination of ketones with weakly nucleophilic sulfonamides has been developed in the presence of a Brønsted acid, giving a wide range of chiral γ-, δ-, and ε-sultams in high yields and up to 99% of enantioselectivity.
Co-reporter:Ji Zhou, Mao-Lin Wang, Xiang Gao, Guo-Fang Jiang and Yong-Gui Zhou
Chemical Communications 2017 - vol. 53(Issue 25) pp:NaN3534-3534
Publication Date(Web):2017/03/07
DOI:10.1039/C7CC01072A
A bifunctional squaramide-catalyzed reaction of azlactones with o-quinone methides in situ generated from 2-(1-tosylalkyl)-phenols has been successfully developed under basic conditions, providing an efficient and mild access to chiral dihydrocoumarins bearing adjacent tertiary and quaternary stereogenic centers in high yields with excellent diastereo- and enantioselectivities.
Co-reporter:Zhong Yan, Bo Wu, Xiang Gao and Yong-Gui Zhou
Chemical Communications 2016 - vol. 52(Issue 72) pp:NaN10885-10885
Publication Date(Web):2016/08/09
DOI:10.1039/C6CC04096A
A highly enantioselective addition of arylboronic acids to cyclic α-ketiminophosphonates is reported using a chiral palladium phosphinooxazoline catalyst, providing an efficient and facile route to quaternary α-aminophosphonates in high yields and up to 99.9% enantioselectivity.
Co-reporter:Yue Ji, Guang-Shou Feng, Mu-Wang Chen, Lei Shi, Haifeng Du and Yong-Gui Zhou
Inorganic Chemistry Frontiers 2017 - vol. 4(Issue 6) pp:NaN1129-1129
Publication Date(Web):2017/02/24
DOI:10.1039/C7QO00060J
An enantioselective hydrogenation of cyclic iminium salts has been successfully realized by employing [Ir(COD)Cl]2 and chiral diphosphine ligands as catalyst, furnishing chiral N-alkyl tetrahydroisoquinolines and N-alkyl tetrahydro-β-carbolines with up to 96% ee and 88% ee, respectively. The hydrogenation provides a direct, simple and efficient protocol toward chiral tertiary amines. Meanwhile, asymmetric hydrogenation at the gram scale was also conducted smoothly without loss of reactivity and enantioselectivity.
Co-reporter:Mu-Wang Chen, Zhi-Shi Ye, Zhang-Pei Chen, Bo Wu and Yong-Gui Zhou
Inorganic Chemistry Frontiers 2015 - vol. 2(Issue 5) pp:NaN589-589
Publication Date(Web):2015/03/31
DOI:10.1039/C5QO00069F
An enantioselective iridium-catalyzed hydrogenation of trifluoromethyl substituted pyridinium hydrochlorides is described. Introduction of a trifluoromethyl group increases the reactivity due to the electron-withdrawing effect. Three stereogenic centers could be generated in one operation. This methodology provides a convenient route to chiral poly-substituted piperidines with up to 90% ee.
Co-reporter:Xian-Feng Cai, Wen-Xue Huang, Zhang-Pei Chen and Yong-Gui Zhou
Chemical Communications 2014 - vol. 50(Issue 67) pp:NaN9590-9590
Publication Date(Web):2014/07/04
DOI:10.1039/C4CC04386C
Homogeneous Pd-catalyzed asymmetric hydrogenation of 3-phthalimido substituted quinolines was successfully developed, providing facile access to chiral substituted tetrahydroquinolines bearing two contiguous stereogenic centers with up to 90% ee.
Co-reporter:Mu-Wang Chen, Liang-Liang Cao, Zhi-Shi Ye, Guo-Fang Jiang and Yong-Gui Zhou
Chemical Communications 2013 - vol. 49(Issue 16) pp:NaN1662-1662
Publication Date(Web):2013/01/08
DOI:10.1039/C3CC37800D
A novel and efficient method for the generation of o-quinone methide intermediates was developed from the readily available 2-tosylalkylphenols under the mild basic conditions, and their reactions with sulfur ylides were investigated for the stereoselective synthesis of trans-2,3-dihydrobenzofurans.
Co-reporter:Mu-Wang Chen, Qing-An Chen, Ying Duan, Zhi-Shi Ye and Yong-Gui Zhou
Chemical Communications 2012 - vol. 48(Issue 11) pp:NaN1700-1700
Publication Date(Web):2011/12/06
DOI:10.1039/C2CC16832D
Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones, was developed using chiral phosphoric acid as catalyst and a Hantzsch ester as the hydrogen source with up to 95% ee. The reaction process of this asymmetric transfer hydrogenation may occur directly through the acyliminium ion intermediate.
Co-reporter:Mu-Wang Chen, Xian-Feng Cai, Zhang-Pei Chen, Lei Shi and Yong-Gui Zhou
Chemical Communications 2014 - vol. 50(Issue 83) pp:NaN12529-12529
Publication Date(Web):2014/08/29
DOI:10.1039/C4CC06060A
An efficient and facile route to chiral tetrahydroquinolines with three contiguous stereogenic centers via a dynamic kinetic resolution process has been successfully developed by using chiral phosphoric acid as catalyst and Hantzsch ester as the hydrogen source with up to 89% ee.
Co-reporter:Kai Gao, Chang-Bin Yu, Wei Li, Yong-Gui Zhou and Xumu Zhang
Chemical Communications 2011 - vol. 47(Issue 27) pp:NaN7847-7847
Publication Date(Web):2011/05/31
DOI:10.1039/C1CC12263K
Highly enantioselective hydrogenation of seven-membered cyclic imines, substituted dibenzo[b,f][1,4]oxazepines, was achieved, with up to 94% ee, by using the [Ir(COD)Cl]2/(S)-Xyl-C3*-TunePhos complex as the catalyst in the presence of morpholine-HCl.
Co-reporter:Ran-Ning Guo, Xian-Feng Cai, Lei Shi, Zhi-Shi Ye, Mu-Wang Chen and Yong-Gui Zhou
Chemical Communications 2013 - vol. 49(Issue 76) pp:NaN8539-8539
Publication Date(Web):2013/07/22
DOI:10.1039/C3CC45341C
An efficient iridium-catalyzed asymmetric hydrogenation of the fluorinated isoquinoline derivatives has been successfully developed for the synthesis of chiral fluorinated tetrahydroisoquinoline derivatives with up to 93% ee. This methodology features the use of a hydrochloride salt as well as a catalytic amount of halogenated hydantoin which were vital for the reactivity, enantioselectivity, and inhibition of the hydrodefluorination pathway.
Co-reporter:Long-Wu Ye, Shou-Bing Wang, Qing-Gang Wang, Xiu-Li Sun, Yong Tang and Yong-Gui Zhou
Chemical Communications 2009(Issue 21) pp:NaN3094-3094
Publication Date(Web):2009/04/15
DOI:10.1039/B900048H
The reaction of a crotonate-derived chiral phosphonium salt with α,β-unsaturated carbonyl compounds in the presence of Cs2CO3 affords optically active cyclohexa-1,3-diene derivatives with up to 90% ee in good yields.
Co-reporter:Chang-Bin Yu, Kao Gao, Duo-Sheng Wang, Lei Shi and Yong-Gui Zhou
Chemical Communications 2011 - vol. 47(Issue 17) pp:NaN5054-5054
Publication Date(Web):2011/03/24
DOI:10.1039/C1CC10313J
Asymmetric hydrogenation of cyclic enesulfonamides affords chiral cyclic sulfonamides using Pd(OCOCF3)2/diphosphine complexes as catalysts with up to 98% ee.
Co-reporter:Qing-An Chen, Duo-Sheng Wang and Yong-Gui Zhou
Chemical Communications 2010 - vol. 46(Issue 23) pp:NaN4051-4051
Publication Date(Web):2010/05/11
DOI:10.1039/C001089H
The discovery and progress of new bifunctional AgOAc-based catalysts for asymmetric reactions is described. In this bifunctional procedure, AgOAc acts as an efficient Lewis acid catalyst as well as a base through the deprotonation of active hydrogen promoted by acetate. The bifunctional strategy offers a great opportunity to establish new fundamentals for stereoselective construction of C–C as well as C–N bonds.
Co-reporter:Qing-An Chen, Zhi-Shi Ye, Ying Duan and Yong-Gui Zhou
Chemical Society Reviews 2013 - vol. 42(Issue 2) pp:NaN511-511
Publication Date(Web):2012/11/09
DOI:10.1039/C2CS35333D
The transition metal catalyzed asymmetric hydrogenation of unsaturated compounds arguably presents one of the most attractive methods for the synthesis of chiral compounds. Over the last few decades, Pd has gradually grown up as a new and popular metal catalyst in homogeneous asymmetric hydrogenation the same as traditional Ru, Rh and Ir catalysts. Much progress has been successfully achieved in the asymmetric reduction of imines, enamines, olefins, ketones and heteroarenes. It was also found that palladium catalyzed asymmetric hydrogenation could be used as a key step in tandem reactions to quickly synthesize chiral compounds. This tutorial review intends to offer an overview of recent progress in homogeneous palladium catalyzed asymmetric hydrogenation and should serve as an inspiration for further advances in this area.
Co-reporter:Duo-Sheng Wang, Jie Tang, Yong-Gui Zhou, Mu-Wang Chen, Chang-Bin Yu, Ying Duan and Guo-Fang Jiang
Chemical Science (2010-Present) 2011 - vol. 2(Issue 4) pp:NaN806-806
Publication Date(Web):2011/01/24
DOI:10.1039/C0SC00614A
Highly enantioselective hydrogenation of 3-(α-hydroxyalkyl)indoles promoted by a Brønsted acid for dehydration to form a vinylogous iminium intermediate in situ was developed with Pd(OCOCF3)2/(R)-H8-BINAP as catalyst with up to 97% ee. This methodology provides an efficient and rapid access to chiral 2,3-disubstituted indolines.
Co-reporter:Xiang Gao, Bo Wu, Zhong Yan and Yong-Gui Zhou
Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 1) pp:NaN58-58
Publication Date(Web):2015/11/24
DOI:10.1039/C5OB02330K
With the aid of an axially chiral 2,2′-bipyridine ligand, we have successfully developed a palladium-catalyzed method for the enantioselective arylation of N-tosylarylimines, furnishing the chiral diarylmethamines with high yields and enantioselectivities under very mild conditions. An exogenous base was avoided and imine hydrolysis was inhibited in this transformation.
Co-reporter:Ying Duan, Mu-Wang Chen, Qing-An Chen, Chang-Bin Yu and Yong-Gui Zhou
Organic & Biomolecular Chemistry 2012 - vol. 10(Issue 6) pp:NaN1238-1238
Publication Date(Web):2011/11/17
DOI:10.1039/C1OB06777J
A series of 2-substituted 3-(toluenesulfonamidoalkyl)indoles was synthesized by application of (EtO)2POH or iodine as the catalyst, and was hydrogenated using chiral Pd catalyst, giving the 2,3-disubstituted indolines with up to 97% ee.
![BENZENAMINE, 4-METHOXY-N-[3-PHENYL-1-(TRIFLUOROMETHYL)-2-PROPYNYL]-](http://img.cochemist.com/ccimg/850800/850786-05-9.png)
![BENZENAMINE, 4-METHOXY-N-[3-PHENYL-1-(TRIFLUOROMETHYL)-2-PROPYNYL]-](http://img.cochemist.com/ccimg/850800/850786-05-9_b.png)
![Benzenamine, 4-methoxy-N-[1-(trifluoromethyl)-2-heptynyl]-](http://img.cochemist.com/ccimg/850800/850786-04-8.png)
![Benzenamine, 4-methoxy-N-[1-(trifluoromethyl)-2-heptynyl]-](http://img.cochemist.com/ccimg/850800/850786-04-8_b.png)
![(R)-1-[(1S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI-TERT-BUTYLPHOSPHINE](http://img.cochemist.com/ccimg/155900/155830-69-6.png)
![(R)-1-[(1S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI-TERT-BUTYLPHOSPHINE](http://img.cochemist.com/ccimg/155900/155830-69-6_b.png)
![Ferrocene,1-[(1R)-1-(dicyclohexylphosphino)ethyl]-2-(diphenylphosphino)-, (2R)-](http://img.cochemist.com/ccimg/155900/155806-35-2.png)
![Ferrocene,1-[(1R)-1-(dicyclohexylphosphino)ethyl]-2-(diphenylphosphino)-, (2R)-](http://img.cochemist.com/ccimg/155900/155806-35-2_b.png)
![4-Phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazin-2-one](http://img.cochemist.com/ccimg/1129300/1129278-73-4.png)
![4-Phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazin-2-one](http://img.cochemist.com/ccimg/1129300/1129278-73-4_b.png)
![2H-1,4-BENZOXAZINE, 3-[1,1'-BIPHENYL]-4-YL-3,4-DIHYDRO-, (3R)-](http://img.cochemist.com/ccimg/917100/917085-38-2.png)
![2H-1,4-BENZOXAZINE, 3-[1,1'-BIPHENYL]-4-YL-3,4-DIHYDRO-, (3R)-](http://img.cochemist.com/ccimg/917100/917085-38-2_b.png)
![CARBAMIC ACID, [(3-OXO-3-PHENYLPROPYL)SULFONYL]-, 1,1-DIMETHYLETHYL ESTER](http://img.cochemist.com/ccimg/881700/881652-44-4.png)
![CARBAMIC ACID, [(3-OXO-3-PHENYLPROPYL)SULFONYL]-, 1,1-DIMETHYLETHYL ESTER](http://img.cochemist.com/ccimg/881700/881652-44-4_b.png)
![N-[3,5-Bis(trifluoromethyl)phenyl]-N-[(8a,9S)-6-methoxy-9-cinchonanyl]thiourea](/data/chemimg/103500/852913-16-7.png)
![N-[3,5-Bis(trifluoromethyl)phenyl]-N-[(8a,9S)-6-methoxy-9-cinchonanyl]thiourea](/data/chemimg/103500/852913-16-7_b.png)
![BENZENESULFONAMIDE, N-[(S)-(2-METHOXYPHENYL)PHENYLMETHYL]-4-METHYL-](http://img.cochemist.com/ccimg/797000/796966-20-6.png)
![BENZENESULFONAMIDE, N-[(S)-(2-METHOXYPHENYL)PHENYLMETHYL]-4-METHYL-](http://img.cochemist.com/ccimg/797000/796966-20-6_b.png)
![BENZENESULFONAMIDE, N-[(S)-(4-METHOXYPHENYL)PHENYLMETHYL]-4-METHYL-](http://img.cochemist.com/ccimg/797000/796966-18-2.png)
![BENZENESULFONAMIDE, N-[(S)-(4-METHOXYPHENYL)PHENYLMETHYL]-4-METHYL-](http://img.cochemist.com/ccimg/797000/796966-18-2_b.png)
![Benzenesulfonamide, N-[(S)-(4-chlorophenyl)phenylmethyl]-4-methyl-](http://img.cochemist.com/ccimg/797000/796966-17-1.png)
![Benzenesulfonamide, N-[(S)-(4-chlorophenyl)phenylmethyl]-4-methyl-](http://img.cochemist.com/ccimg/797000/796966-17-1_b.png)
![BENZENESULFONAMIDE, 4-METHYL-N-[(S)-(4-METHYLPHENYL)PHENYLMETHYL]-](http://img.cochemist.com/ccimg/738700/738626-18-1.png)
![BENZENESULFONAMIDE, 4-METHYL-N-[(S)-(4-METHYLPHENYL)PHENYLMETHYL]-](http://img.cochemist.com/ccimg/738700/738626-18-1_b.png)
![Cyclohexanone, 3-[4-(trifluoromethyl)phenyl]-, (3R)-](http://img.cochemist.com/ccimg/610300/610273-87-5.png)
![Cyclohexanone, 3-[4-(trifluoromethyl)phenyl]-, (3R)-](http://img.cochemist.com/ccimg/610300/610273-87-5_b.png)
](/data/chemimg/2166400/445467-61-8.png)
](/data/chemimg/2166400/445467-61-8_b.png)
![Pyrazine, [4-(trifluoromethyl)phenyl]-](http://img.cochemist.com/ccimg/380700/380626-88-0.png)
![Pyrazine, [4-(trifluoromethyl)phenyl]-](http://img.cochemist.com/ccimg/380700/380626-88-0_b.png)
![Pyrazine, [1,1'-biphenyl]-4-yl-](http://img.cochemist.com/ccimg/377100/377047-39-7.png)
![Pyrazine, [1,1'-biphenyl]-4-yl-](http://img.cochemist.com/ccimg/377100/377047-39-7_b.png)
![Phosphine,1,1'-[(1R)-5,5'-dichloro-6,6'-dimethoxy[1,1'-biphenyl]-2,2'-diyl]bis[1,1-diphenyl-](/data/chemimg/110700/185913-97-7.png)
![Phosphine,1,1'-[(1R)-5,5'-dichloro-6,6'-dimethoxy[1,1'-biphenyl]-2,2'-diyl]bis[1,1-diphenyl-](/data/chemimg/110700/185913-97-7_b.png)
![Sulfonium, [2-(diethylamino)-2-oxoethyl]dimethyl-, bromide](http://img.cochemist.com/ccimg/146900/146839-13-6.png)
![Sulfonium, [2-(diethylamino)-2-oxoethyl]dimethyl-, bromide](http://img.cochemist.com/ccimg/146900/146839-13-6_b.png)
![Benzenesulfonamide, N-[(3,4-dimethoxyphenyl)methylene]-4-methyl-,(E)-](http://img.cochemist.com/ccimg/137900/137845-39-7.png)
![Benzenesulfonamide, N-[(3,4-dimethoxyphenyl)methylene]-4-methyl-,(E)-](http://img.cochemist.com/ccimg/137900/137845-39-7_b.png)
![1-Chloropyrrolo[1,2-a]pyrazine](http://img.cochemist.com/ccimg/137000/136927-64-5.png)
![1-Chloropyrrolo[1,2-a]pyrazine](http://img.cochemist.com/ccimg/137000/136927-64-5_b.png)
![Cyclohexanone, 3-[4-(trifluoromethyl)phenyl]-](http://img.cochemist.com/ccimg/123000/122902-06-1.png)
![Cyclohexanone, 3-[4-(trifluoromethyl)phenyl]-](http://img.cochemist.com/ccimg/123000/122902-06-1_b.png)
![Oxaziridine, 3-methyl-2-[(4-methylphenyl)sulfonyl]-3-phenyl-](http://img.cochemist.com/ccimg/118700/118616-91-4.png)
![Oxaziridine, 3-methyl-2-[(4-methylphenyl)sulfonyl]-3-phenyl-](http://img.cochemist.com/ccimg/118700/118616-91-4_b.png)
![Pyrrolo[1,2-a]pyrazine, 1-(4-chlorophenyl)-](http://img.cochemist.com/ccimg/112800/112758-97-1.png)
![Pyrrolo[1,2-a]pyrazine, 1-(4-chlorophenyl)-](http://img.cochemist.com/ccimg/112800/112758-97-1_b.png)
![Phosphonic acid, P-[[[(4-methylphenyl)sulfonyl]amino]phenylmethyl]-, diethyl ester](/data/chemimg/3740200/84454-05-7.png)
![Phosphonic acid, P-[[[(4-methylphenyl)sulfonyl]amino]phenylmethyl]-, diethyl ester](/data/chemimg/3740200/84454-05-7_b.png)
![3-Methyl-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide](http://img.cochemist.com/ccimg/84200/84108-98-5.png)
![3-Methyl-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide](http://img.cochemist.com/ccimg/84200/84108-98-5_b.png)
![Benzenesulfonamide, 4-methyl-N-[(1R)-1-phenylethyl]-](http://img.cochemist.com/ccimg/73000/72984-27-1.png)
![Benzenesulfonamide, 4-methyl-N-[(1R)-1-phenylethyl]-](http://img.cochemist.com/ccimg/73000/72984-27-1_b.png)
![Benzenesulfonamide, 4-methyl-N-[(S)-1-naphthalenylphenylmethyl]-](http://img.cochemist.com/ccimg/66600/66558-07-4.png)
![Benzenesulfonamide, 4-methyl-N-[(S)-1-naphthalenylphenylmethyl]-](http://img.cochemist.com/ccimg/66600/66558-07-4_b.png)
![1-Methylpyrrolo[1,2-a]pyrazine](http://img.cochemist.com/ccimg/64700/64608-59-9.png)
![1-Methylpyrrolo[1,2-a]pyrazine](http://img.cochemist.com/ccimg/64700/64608-59-9_b.png)
![(6E)-6-[(4-methoxyphenyl)methylidene]-1,3-benzodioxol-5(6H)-one](http://img.cochemist.com/ccimg/63200/63194-80-9.png)
![(6E)-6-[(4-methoxyphenyl)methylidene]-1,3-benzodioxol-5(6H)-one](http://img.cochemist.com/ccimg/63200/63194-80-9_b.png)
![PHENOL, 4,5-DIMETHOXY-2-[(4-METHOXYPHENYL)METHYL]-](http://img.cochemist.com/ccimg/63200/63194-79-6.png)
![PHENOL, 4,5-DIMETHOXY-2-[(4-METHOXYPHENYL)METHYL]-](http://img.cochemist.com/ccimg/63200/63194-79-6_b.png)
![Pyrazino[2,1-a]pyrido[2,3-c][2]benzazepine,1,2,3,4,10,14b-hexahydro-2-methyl-, (14bS)-](http://img.cochemist.com/ccimg/61400/61337-87-9.png)
![Pyrazino[2,1-a]pyrido[2,3-c][2]benzazepine,1,2,3,4,10,14b-hexahydro-2-methyl-, (14bS)-](http://img.cochemist.com/ccimg/61400/61337-87-9_b.png)
![4,5-dihydro-Pyrrolo[1,2-a]quinoxaline](http://img.cochemist.com/ccimg/56800/56721-86-9.png)
![4,5-dihydro-Pyrrolo[1,2-a]quinoxaline](http://img.cochemist.com/ccimg/56800/56721-86-9_b.png)
![Pyrrolo[1,2-a]pyrazine, 1-phenyl-](http://img.cochemist.com/ccimg/39600/39573-69-8.png)
![Pyrrolo[1,2-a]pyrazine, 1-phenyl-](http://img.cochemist.com/ccimg/39600/39573-69-8_b.png)
![2H-1,4-Benzoxazine, 3-[1,1'-biphenyl]-4-yl-](http://img.cochemist.com/ccimg/32700/32683-64-0.png)
![2H-1,4-Benzoxazine, 3-[1,1'-biphenyl]-4-yl-](http://img.cochemist.com/ccimg/32700/32683-64-0_b.png)
![1H-Indole,2-[(1E)-2-phenylethenyl]-](http://img.cochemist.com/ccimg/29500/29475-88-5.png)
![1H-Indole,2-[(1E)-2-phenylethenyl]-](http://img.cochemist.com/ccimg/29500/29475-88-5_b.png)
![Spiro[1,3-dioxolane-2,1'(4'H)-naphthalen]-4'-one](http://img.cochemist.com/ccimg/6600/6541-89-5.png)
![Spiro[1,3-dioxolane-2,1'(4'H)-naphthalen]-4'-one](http://img.cochemist.com/ccimg/6600/6541-89-5_b.png)
![1H-Indole, 3-[(4-methoxyphenyl)methyl]-2-methyl-](http://img.cochemist.com/ccimg/5800/5782-24-1.png)
![1H-Indole, 3-[(4-methoxyphenyl)methyl]-2-methyl-](http://img.cochemist.com/ccimg/5800/5782-24-1_b.png)
![Oxirane,2-[(2-naphthalenyloxy)methyl]-](http://img.cochemist.com/ccimg/5300/5234-06-0.png)
![Oxirane,2-[(2-naphthalenyloxy)methyl]-](http://img.cochemist.com/ccimg/5300/5234-06-0_b.png)
![Oxirane,2-[(4-methylphenoxy)methyl]-](http://img.cochemist.com/ccimg/2200/2186-24-5.png)
![Oxirane,2-[(4-methylphenoxy)methyl]-](http://img.cochemist.com/ccimg/2200/2186-24-5_b.png)
![Pyrrolo[1,2-a]quinoxaline](http://img.cochemist.com/ccimg/300/234-95-7.png)
![Pyrrolo[1,2-a]quinoxaline](http://img.cochemist.com/ccimg/300/234-95-7_b.png)
