Yungui Peng

Name: 彭云贵

Organization: Southwest University , China

Department: School of Chemistry and Chemical Engineering

Title: NULL(PhD)

Chemicals
References

Enantioselective 1,3-Dipolar Cycloaddition of Methyleneindolinones with α-Diazomethylphosphonate to Access Chiral Spiro-phosphonylpyrazoline-oxindoles Catalyzed by Tertiary Amine Thiourea and 1,5-Diazabicyclo[4.3.0]non-5-ene

Co-reporter:Nan Huang, Liangliang Zou, and Yungui Peng

Organic Letters November 3, 2017 Volume 19(Issue 21) pp:5806-5806

Publication Date(Web):October 18, 2017

DOI:10.1021/acs.orglett.7b02763

A methodology to access chiral 3,3′-spiro-phosphonylpyrazoline oxindoles via an asymmetric 1,3-dipolar cycloaddition reaction of substituted methyleneindolinones with α-diazomethylphosphonate in the catalysis of tertiary amine thiourea and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) has been established. This method exhibits high functional group compatibility, where a wide range of methyleneindolinones with various substituents and heterocyclic rings are accommodated by this reaction. The resulting chiral 3,3′-spiro-phosphonylpyrazoline oxindoles can be further transformed into spiro-phosphonylcyclopropane oxindoles by ring contraction.

Asymmetric Reaction of α-Diazomethylphosphonates with α-Ketoesters To Access Optically Active α-Diazo-β-hydroxyphosphonate Derivatives

Co-reporter:Fei Du, Jiao Zhou, and Yungui Peng

Organic Letters March 17, 2017 Volume 19(Issue 6) pp:

Publication Date(Web):February 24, 2017

DOI:10.1021/acs.orglett.7b00128

The first example for asymmetric reaction of diazomethylphosphonates with α-ketoesters was realized in the catalysis of hydroquinidine-derived bifunctional thiourea. A methodology was established to access a series of chiral α-diazo-β-hydroxyphosphonate derivatives containing various functional groups with high enantioselectivities and yields. The resulting products could be further transformed into chiral tertiary β-hydroxyphosphonate and α-halogenated fosfomycin derivatives, especially α-fluoride analogues.

Enantioselective Sulfa-Michael Addition of Aromatic Thiols to β-Substituted Nitroalkenes Promoted by a Chiral Multifunctional Catalyst

Co-reporter:Qi Wei;Wenduan Hou;Na Liao

Advanced Synthesis & Catalysis 2017 Volume 359(Issue 14) pp:2364-2368

Publication Date(Web):2017/07/17

DOI:10.1002/adsc.201700109

AbstractAn efficient enantioselective Michael addition of a series of aromatic thiols acting as nucleophiles for β-monosubstituted, α,β- and β,β-disubstituted nitroalkenes promoted by a multi-functional chiral catalyst has been developed. The methodology accommodates a wide variety of aryl thiols and nitroalkene substrates, and affords the 2-nitro-1-arylethyl sulfides in excellent yields (up to 99%) and enantioselectivities (up to 99% ee). This reaction could be scaled up to gram even with a dramatically reduced catalyst loading of 0.05 mol%.

Asymmetric Mannich Reaction of Isatin-Based Ketimines with α-Diazomethylphosphonates Catalyzed by Chiral Silver Phosphate

Co-reporter:Jing Chen, Xiaojing Wen, Yan Wang, Fei Du, Liu Cai, and Yungui Peng

Organic Letters 2016 Volume 18(Issue 17) pp:4336-4339

Publication Date(Web):August 23, 2016

DOI:10.1021/acs.orglett.6b02095

An efficient asymmetric Mannich reaction of isatin-based ketimines with α-diazomethylphosphonates has been developed using a chiral binaphthanol-derived silver phosphate as the catalyst. This reaction allowed the construction of a series of chiral oxindoles bearing a quaternary stereocenter and amino group at the C3 position with up to 95% yields and 99% ee. Those products could be further transformed into promising densely functionalized compounds by merging of the oxindole and β-aminophosphonate.

An Enantioselective Three-Component Sulfa-Michael/Aldol Cascade Reaction and its Application to the Synthesis of Thioaryl Substituted ()-Bestatin Derivatives

Co-reporter:Wenduan Hou;Qi Wei

Advanced Synthesis & Catalysis 2016 Volume 358( Issue 7) pp:1035-1041

Publication Date(Web):

DOI:10.1002/adsc.201600026

Catalytic Asymmetric Synthesis of Phosphoryl-1,4-dihydropyridazines via an Enantioselective Allylic Alkylation/1,3-Dipolar Cycloaddition/Rearrangement Reaction Sequence

Co-reporter:Fei Du;Liyang Yin;Yanqiang Ning

Advanced Synthesis & Catalysis 2016 Volume 358( Issue 14) pp:2280-2285

Publication Date(Web):

DOI:10.1002/adsc.201600353

A Cation-Directed Enantioselective Sulfur-Mediated Michael/Mannich Three-Component Domino Reaction involving Chalcones as Michael Acceptors

Co-reporter:Ran Ding, Bo Zheng, Yan Wang, and Yungui Peng

Organic Letters 2015 Volume 17(Issue 17) pp:4128-4131

Publication Date(Web):August 21, 2015

DOI:10.1021/acs.orglett.5b01833

A new approach has been developed for an asymmetric sulfur-mediated three-component intermolecular Michael/Mannich domino reaction using chalcones as Michael acceptors. This reaction is catalyzed by chiral quaternary ammonium salts derived from modified quinine and provides facile access to complex sulfur-containing compounds with three contiguous stereogenic centers in yields of up to 93%, with 95:5 dr and 95% ee. These compounds were further elaborated to give the equivalent of a chiral aza-Morita–Baylis–Hillman reaction involving chalcones and azetidines bearing four chiral centers.

Organocatalytic Enantioselective 1,3-Dipolar Cycloadditions between Seyferth–Gilbert Reagent and Isatylidene Malononitriles: Synthesis of Chiral Spiro-phosphonylpyrazoline-oxindoles

Co-reporter:Taiping Du, Fei Du, Yanqiang Ning, and Yungui Peng

Organic Letters 2015 Volume 17(Issue 5) pp:1308-1311

Publication Date(Web):February 24, 2015

DOI:10.1021/acs.orglett.5b00311

A new method has been developed for the catalytic enantioselective 1,3-dipolar cycloaddition of the Seyferth–Gilbert reagent (SGR) to isatylidene malononitriles using a cinchona alkaloid derivative as a catalyst. This method allowed for the synthesis of a series of chiral spiro-phosphonylpyrazoline-oxindoles in good yields with excellent enantioselectivities. The synthetic utility of this method was further demonstrated by its use in a three-component domino reaction involving isatin, malononitrile, and SGR based on sequential Knoevenagel condensation and 1,3-dipolar cycloaddition reactions.

Asymmetric Multicomponent Sulfa-Michael/Mannich Cascade Reaction: Synthetic Access to 1,2-Diamino-3-Organosulfur Compounds and 2-Nitro Allylic Amines

Co-reporter:Wenduan Hou, Qi Wei, Guisheng Liu, Jing Chen, Jing Guo, and Yungui Peng

Organic Letters 2015 Volume 17(Issue 19) pp:4870-4873

Publication Date(Web):September 16, 2015

DOI:10.1021/acs.orglett.5b02423

A novel catalytic asymmetric three-component intermolecular sulfa-Michael/Mannich cascade reaction has been developed using a chiral multifunctional catalyst. This reaction provides facile access to 1-amino-2-nitro-3-organosulfur compounds bearing three consecutive stereocenters in high yields (up to 96%) with good diastereo- (up to 91:4:4:1 dr) and excellent enantioselectivities (93–99% ee). Furthermore, the products of this reaction could be facilely transformed into potentially bioactive 1, 2-diamino-3-organosulfur compounds and 2-nitro allylic amines.

Construction of Chiral 2-Substituted Octahydroindoles from Cyclic Ketones and Nitroolefins Bearing only One -Substituent

Co-reporter:Yong Han;Bo Zheng

Advanced Synthesis & Catalysis 2015 Volume 357( Issue 6) pp:1136-1142

Publication Date(Web):

DOI:10.1002/adsc.201400851

Synthesis of Multifunctional 3-Amino-4-phosphono-2-quinolinones via Regioselective Ring Enlargement of Imino Isatins

Co-reporter:Xiaojing Wen;Jing Chen

Advanced Synthesis & Catalysis 2014 Volume 356( Issue 18) pp:3794-3798

Publication Date(Web):

DOI:10.1002/adsc.201400652

Asymmetric oxa-Michael-aza-Henry Cascade Reaction of 2-Hydroxyaryl-Substituted -Amido Sulfones and Nitroolefins Mediated by Chiral Squaramides

Co-reporter:Dr. Bo Zheng;Dr. Wenduan Hou ; Yungui Peng

ChemCatChem 2014 Volume 6( Issue 9) pp:2527-2530

Publication Date(Web):

DOI:10.1002/cctc.201402236

Abstract

A series of chiral squaramides were employed in the oxa-Michael-aza-Henry cascade reaction of 2-hydroxyaryl-substituted α-amido sulfones and nitroolefins. In the presence of 10 mol % of a squaramide catalyst and K₂CO₃ (aq) in CHCl₃ at 0 °C, this reaction proceeded smoothly to afford chiral multisubstituted 4-amino-3-nitrobenzopyrans, bearing a readily removable N-Boc protecting group (Boc=tert-butoxycarbonyl), in excellent yields (up to 98 %) and enantioselectivity [up to 98:2 enantiomeric ratio (er) and 93:7 diastereomeric ratio (dr)]. The 4-amino-3-nitrobenzopyrans were converted into chiral 3,4-diamino chromanes, which were further exploited as chiral ligands in the asymmetric transfer hydrogenation of acetophenone, providing 1-phenylethanol in up to 84 % yield and 93.5:6.5 er.

A novel method to access chiral nonnatural 2,4-disubstituted pyrrolidines from aldehydes and nitroolefins only with an α-substituent

Co-reporter:Bo Zheng, Hui Wang, Yong Han, Changlu Liu and Yungui Peng

Chemical Communications 2013 vol. 49(Issue 40) pp:4561-4563

Publication Date(Web):26 Mar 2013

DOI:10.1039/C3CC40583D

A series of α-substituted nitroolefins were employed in organocatalytic asymmetric Michael reactions with aldehydes. γ-Nitro carbonyl products were achieved in good yields (up to 86%) with good stereoselectivities (up to 96% ee and 24:1 dr). Reduction of the nitro group followed by intramolecular reductive amination successfully afforded various novel optically active 2,4-disubstituted pyrrolidine compounds.

3-Bromooxindoles as nucleophiles in asymmetric organocatalytic Mannich reactions with N-Ts-imines

Co-reporter:Jianhao Li, Taiping Du, Gang Zhang and Yungui Peng

Chemical Communications 2013 vol. 49(Issue 13) pp:1330-1332

Publication Date(Web):19 Dec 2012

DOI:10.1039/C2CC38475B

A direct asymmetric Mannich reaction of N-unprotected 3-bromooxindoles with N-Ts-imines catalyzed by bifunctional thiourea derived from 2-substituted cinchona alkaloid was developed. Products with vicinal chiral tertiary and brominated quaternary stereogenic centers were achieved in excellent diastereo- and enantioselectivity (up to 99:1 dr, 99% ee).

Asymmetric Synthesis of Polysubstituted 4-Amino- and 3,4-Diaminochromanes with a Chiral Multifunctional Organocatalyst

Co-reporter:Wenduan Hou, Bo Zheng, Jun Chen, and Yungui Peng

Organic Letters 2012 Volume 14(Issue 9) pp:2378-2381

Publication Date(Web):April 12, 2012

DOI:10.1021/ol300798t

A series of multifunctional catalysts with two chiral diaminocyclohexane units were developed and successfully applied in the asymmetric oxa-Michael–aza-Henry cascade reaction of salicylaldimines with nitroolefins. This approach provides a simple and efficient entry to polysubstituted chiral 4-aminobenzopyrans with three consecutive stereocenters and in high yield (up to 97%) with excellent stereoselectivity (up to 98% ee and >99:1 dr). Facile access to the nonsymmetric optically pure 3,4-diaminochromanes was also obtained.

Highly Efficient Asymmetric Mannich Reaction of Dialkyl α-Diazomethylphosphonates with N-Carbamoyl Imines Catalyzed by Chiral Brønsted Acids

Co-reporter:Hui Zhang, Xiaojing Wen, Lihua Gan, and Yungui Peng

Organic Letters 2012 Volume 14(Issue 8) pp:2126-2129

Publication Date(Web):March 30, 2012

DOI:10.1021/ol300664d

An efficient method involving the first use of chiral phosphoric acids as catalysts in the asymmetric Mannich reaction of dialkyl diazomethylphosphonates and N-carbamoyl imines is developed. With only 0.1 mol % catalyst 1f, the reaction proceeded smoothly and produced the corresponding β-amino-α-diazophosphonate with up to 97% yield and >99% ee.

Highly efficient asymmetric anti-Mannich reactions of carbonyl compounds with N-carbamoyl imines catalyzed by amino-thiourea organocatalysts

Co-reporter:Jiuzhi Gao, Yongming Chuan, Jiali Li, Fang Xie and Yungui Peng

Organic & Biomolecular Chemistry 2012 vol. 10(Issue 18) pp:3730-3738

Publication Date(Web):02 Mar 2012

DOI:10.1039/C2OB00049K

A series of pyrrolidine-based organocatalysts which bear three synergistic features, i.e. secondary amino group, various H-bond donor groups at the 4-position and a stereocontrol silyl ether group at the α-position of the pyrrolidine nitrogen atom, were developed. They were screened in anti-Mannich reactions of carbonyl compounds with preformed or in situ generated N-protected α-imino ethylglyoxylate and aldehydes with preformed or in situ generated N-carbamoyl imines. The influence of H-bond donor ability at the 4-position was also investigated. Among all the catalysts, 2a was identified as a general efficient organocatalyst suitable for various types of anti-Mannich reactions and broad substrate scope. Excellent results (up to 98% yield, >99% ee and >99:1 dr) were achieved with 5 mol% catalyst load. Sulfones with ortho substituents or very strong withdrawing groups on the aromatic ring, which have been regarded as challenging substrates in the direct anti-Mannich reactions of aldehydes with in situ generated N-carbamoyl imines, also worked well. The optimization of our catalytic system also offered alternative and easily operational protocols to access anti-Mannich products with orthogonal N-Boc or N-Cbz protecting groups.

A systematic study of chiral homoprolinols and their derivatives in the catalysis of enantioselective addition of diethylzinc to aldehydes

Co-reporter:Chang-Lu Liu;Chang-Yong Wei;Shi-Wen Wang;Yun-Gui Peng

Chirality 2011 Volume 23( Issue 10) pp:921-928

Publication Date(Web):

DOI:10.1002/chir.21017

Abstract

Homoprolinol analogs, a class of optically active γ-amino alcohols, were examined systematically in the enantioselective addition reactions of diethylzinc to aldehydes. By comparison of the results catalyzed by these γ-amino alcohols with those by the β-amino alcohols based on pyrrolidine architecture reported in the literature references, we have observed that the γ-amino alcohols are superior to the corresponding β-amino alcohols when the nitrogen and the oxygen are unsubstituted. Among the homoprolinols we tested, 2b gave the best results (45–88% yields, 44–81% ee) in the addition reactions. To the best of our knowledge, 2b has been noticed as one of the most efficient γ-amino alcohol catalysts based on pyrrolidine framework. Chirality, 2011. © 2011 Wiley-Liss, Inc.

4-Trifluoromethanesulfonamidyl prolinol tert-butyldiphenylsilyl ether as a highly efficient bifunctional organocatalyst for Michael addition of ketones and aldehydes to nitroolefins

Co-reporter:Chao Wang, Chun Yu, Changlu Liu, Yungui Peng

Tetrahedron Letters 2009 50(20) pp: 2363-2366

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.02.211

Highly enantioselective Michael addition reactions in water catalyzed by an insoluble MPS-supported 4-sulfonamidyl prolinol tert-butyldiphenylsilyl ether

Co-reporter:Yongming Chuan, Guihua Chen, Yungui Peng

Tetrahedron Letters 2009 50(25) pp: 3054-3058

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.04.011

A novel method to access chiral nonnatural 2,4-disubstituted pyrrolidines from aldehydes and nitroolefins only with an α-substituent

Co-reporter:Bo Zheng, Hui Wang, Yong Han, Changlu Liu and Yungui Peng