Hui Lv

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Name: 吕辉; Lv, Hui
Organization: Wuhan University , China
Department: College of Chemistry and Molecular Sciences
Title: Associate Professor(PhD)

TOPICS

Co-reporter:Hailong Yang, Erfei Wang, Ping Yang, Hui Lv, and Xumu Zhang
Organic Letters October 6, 2017 Volume 19(Issue 19) pp:
Publication Date(Web):September 8, 2017
DOI:10.1021/acs.orglett.7b02262
Highly enantioselective pyridine-directed rhodium-catalyzed asymmetric hydrogenation of challenging 1,1-diarylalkenes is achieved by using [Rh(NBD)DuanPhos]BF4 as a precatalyst. Various types of 2-pyridine substituted 1,1-diarylalkenes could be hydrogenated with good to excellent enantioselectivities, which provide an efficient route to the synthesis of pharmaceutically and biologically active compounds containing a 2-pyridyl ethane unit.
Co-reporter:Xiuxiu Li, Cai You, Shuailong Li, Hui Lv, and Xumu Zhang
Organic Letters October 6, 2017 Volume 19(Issue 19) pp:
Publication Date(Web):September 11, 2017
DOI:10.1021/acs.orglett.7b02417
The nickel-catalyzed asymmetric hydrogenation of β-(acylamino)acrylates has been developed, affording chiral β-amino acid derivatives with excellent yields (95–99% yield) and enantioselectivities (97–99% ee). With the Ni–Binapine system, high enantioselectivities (98–99% ee) have also been obtained in the hydrogenation of Z/E isomeric mixtures of β-alkyl and β-aryl β-(acylamino)acrylates. The synthesis of chiral β-amino acid derivatives on a gram scale has also been achieved with 0.2 mol % catalyst loading.
Co-reporter:Liyang Shi;Biao Wei;Peng Xue;Xuguang Yin;Xumu Zhang
Organic Letters March 3, 2017 Volume 19(Issue 5) pp:1024-1027
Publication Date(Web):February 23, 2017
DOI:10.1021/acs.orglett.6b03845
Rh/(S)-(+)-DTBM-Segphos complex catalyzed asymmetric hydrogenation of α-substituted vinyl sulfones has been achieved, furnishing the desired products in high yields and excellent enantioselectivities (>90% yield, up to 99% ee). This method provided an efficient approach to α-substituted chiral sulfones under mild conditions and has potential applications in organic synthesis.
Co-reporter:Wenchao Gao;Tonghuan Zhang;Yuhong Yang;Lung Wa Chung;Yun-Dong Wu;Xumu Zhang
Chemical Science (2010-Present) 2017 vol. 8(Issue 9) pp:6419-6422
Publication Date(Web):2017/08/21
DOI:10.1039/C7SC02669B
An efficient approach for synthesizing chiral β-amino nitroalkanes has been developed via the Ni-catalyzed asymmetric hydrogenation of challenging β-amino nitroolefins under mild conditions, affording the desired products in excellent yields and with high enantioselectivities. This protocol had good compatibility with the wide substrate scope and a range of functional groups. The synthesis of chiral β-amino nitroalkanes on a gram scale has also been achieved. In addition, the reaction mechanism was elucidated using a combined experimental and computational study, and it involved acetate-assisted heterolytic H2 cleavage followed by 1,4-hydride addition and protonation to achieve the nitroalkanes.
Co-reporter:Yu-Qing Guan;Min Gao;Xu Deng;Xumu Zhang
Chemical Communications 2017 vol. 53(Issue 58) pp:8136-8139
Publication Date(Web):2017/07/18
DOI:10.1039/C7CC03902F
A rhodium-catalyzed asymmetric hydrogenation of challenging tetrasubstituted β-acetoxy-α-enamido esters was developed, giving chiral β-acetoxy-α-amido esters in high yields with excellent enantioselectivities (up to >99% ee). The products could be easily transformed to β-hydroxy-α-amino acid derivatives which are valuable chiral building blocks and a novel route for the synthesis of droxidopa was also developed.
Co-reporter:Xiuxiu Li;Cai You;Yusheng Yang;Fangyuan Wang;Shuailong Li;Xumu Zhang
Chemical Communications 2017 vol. 53(Issue 7) pp:1313-1316
Publication Date(Web):2017/01/19
DOI:10.1039/C6CC09662J
An efficient rhodium-catalyzed asymmetric hydrogenation of α-amino acrylonitriles has been developed, affording α-acylamino nitriles with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). This novel methodology provides an efficient and concise synthetic route to chiral α-amino nitriles, which are versatile intermediates in organic synthesis.
Co-reporter:Biao Wei;Caiyou Chen;Cai You;Xumu Zhang
Organic Chemistry Frontiers 2017 vol. 4(Issue 2) pp:288-291
Publication Date(Web):2017/02/01
DOI:10.1039/C6QO00641H
A concise and efficient synthesis of (S,R)-Bn-Yanphos on a gram scale has been developed. When (S,R)-Bn-Yanphos was employed in Rh-catalyzed asymmetric hydroformylation of vinyl heteroarenes and allyl-1H-indole, it exhibited excellent catalytic activity, affording chiral heteroaryl aldehydes in good yields with high regio- and enantioselectivities (up to 96% ee).
Co-reporter:Caiyou Chen; Shicheng Jin; Zhefan Zhang; Biao Wei; Heng Wang; Kai Zhang; Hui Lv; Xiu-Qin Dong;Xumu Zhang
Journal of the American Chemical Society 2016 Volume 138(Issue 29) pp:9017-9020
Publication Date(Web):July 7, 2016
DOI:10.1021/jacs.6b03596
The first interrupted asymmetric hydroaminomethylation reaction was developed. The challenging trans-1,2-disubstituted olefins were employed as substrates, and a series of valuable chiral pyrrolidinones and pyrrolidines were obtained in high yields with high regioselectivities and excellent enantioselectivities. Several synthetic transformations were conducted, demonstrating the high synthetic utility of our method. A creative route for the synthesis of vernakalant and Enablex was also developed.
Co-reporter:Cai You;Biao Wei;Xiuxiu Li;Yusheng Yang;Yue Liu;Dr. Hui Lv;Dr. Xumu Zhang
Angewandte Chemie 2016 Volume 128( Issue 22) pp:6621-6624
Publication Date(Web):
DOI:10.1002/ange.201601478

Abstract

Excellent enantioselectivities (up to 97 % ee) and diastereoselectivities (up to >99:1 d.r.) have been achieved in the desymmetrization of cyclopentenes by catalytic hydroformylation. This novel methodology provides an efficient and concise synthetic route to chiral cyclopentane carboxaldehydes. The key intermediate, (1S,3S)-(3-hydroxymethyl)cyclopentanol, for the synthesis of carbocyclic-ddA was obtained in three steps.

Co-reporter:Cai You;Biao Wei;Xiuxiu Li;Yusheng Yang;Yue Liu;Dr. Hui Lv;Dr. Xumu Zhang
Angewandte Chemie International Edition 2016 Volume 55( Issue 22) pp:6511-6514
Publication Date(Web):
DOI:10.1002/anie.201601478

Abstract

Excellent enantioselectivities (up to 97 % ee) and diastereoselectivities (up to >99:1 d.r.) have been achieved in the desymmetrization of cyclopentenes by catalytic hydroformylation. This novel methodology provides an efficient and concise synthetic route to chiral cyclopentane carboxaldehydes. The key intermediate, (1S,3S)-(3-hydroxymethyl)cyclopentanol, for the synthesis of carbocyclic-ddA was obtained in three steps.

Co-reporter:Fangyuan Wang;Xuefeng Tan; Hui Lv; Xumu Zhang
Chemistry – An Asian Journal 2016 Volume 11( Issue 15) pp:2103-2106
Publication Date(Web):
DOI:10.1002/asia.201600506

Abstract

New bipyridinemethanamine-containing tetradentate ligands and their corresponding ruthenium complexes have been synthesized. The synthesized complexes performed well in the hydrogenation of a variety of esters with high efficiency (TON up to 9700) giving alcohols in good yields.

Co-reporter:Wenchao Gao;Qingli Wang;Yun Xie;Dr. Hui Lv;Dr. Xumu Zhang
Chemistry – An Asian Journal 2016 Volume 11( Issue 2) pp:231-233
Publication Date(Web):
DOI:10.1002/asia.201500892

Abstract

Rhodium/DuanPhos-catalyzed asymmetric hydrogenation of aliphatic α-dehydroamino ketones has been achieved and afforded chiral α-amino ketones in high yields and excellent enantioselectives (up to 99 % ee), which could be reduced further to chiral β-amino alcohols by LiAlH(tBuO)3 with good yields. This protocol provides a readily accessible route for the synthesis of chiral α-amino ketones and chiral β-amino alcohols.

Co-reporter:Xuefeng Tan, Qingli Wang, Yuanhua Liu, Fangyuan Wang, Hui Lv and Xumu Zhang  
Chemical Communications 2015 vol. 51(Issue 61) pp:12193-12196
Publication Date(Web):12 Jun 2015
DOI:10.1039/C5CC04242A
A hydrazine group-containing nitrogen–phosphine ligand and corresponding ruthenium complexes were synthesized. When these complexes were used for hydrogenation of esters, excellent performance was observed (TON up to 17200). A wide substrate scope was suitable for this catalytic system.
Co-reporter:Jingjing Meng, Min Gao, Hui Lv, and Xumu Zhang
Organic Letters 2015 Volume 17(Issue 8) pp:1842-1845
Publication Date(Web):March 26, 2015
DOI:10.1021/acs.orglett.5b00401
Rh/(R,S)-JosiPhos complex-catalyzed asymmetric hydrogenation of o-alkoxy tetrasubstituted enamides has been achieved, and it furnished a set of β-amino alcohol analogues in high yields and excellent enantiomeric excesses (>99% conversion, up to 99% ee).This method provides valuable chiral building blocks in chiral pharmaceuticals and useful motifs for catalysts.
Co-reporter:Jun Jiang, Wenxin Lu, Hui Lv, and Xumu Zhang
Organic Letters 2015 Volume 17(Issue 5) pp:1154-1156
Publication Date(Web):February 16, 2015
DOI:10.1021/acs.orglett.5b00087
Highly enantioselective catalytic asymmetric hydrogenation of α-CF3-enamides has been achieved by employing rhodium–DuanPhos as the catalyst, which provides a readily accessible method for the synthesis of chiral trifluoromethylated amines. The reaction has a broad substrate scope; both aryl- and alkyl-substituted α-CF3-enamides worked smoothly and afford the corresponding chiral amines in high yields and excellent enantioselectivities (up to 99% ee).
Co-reporter:Xuefeng Tan, Yan Wang, Yuanhua Liu, Fangyuan Wang, Liyang Shi, Ka-Ho Lee, Zhenyang Lin, Hui Lv, and Xumu Zhang
Organic Letters 2015 Volume 17(Issue 3) pp:454-457
Publication Date(Web):January 12, 2015
DOI:10.1021/ol503456j
A new tetradentate ruthenium complex has been developed for hydrogenation of esters. The catalyst’s structure features a pyridinemethanamino group and three tight chelating five-membered rings. The structure character is believed to be responsible for its high stability and high carbonylation-resistant properties. Thus, this catalyst shows outstanding performance in the catalytic hydrogenation of a variety of esters, especially for fatty acid esters, which may be used in practical applications. New insight on designing hydrogenation catalyst for reducing esters to alcohols has been provided through theoretical calculations.
Co-reporter:Hailong Yang, Ningning Huo, Ping Yang, Hao Pei, Hui Lv, and Xumu Zhang
Organic Letters 2015 Volume 17(Issue 17) pp:4144-4147
Publication Date(Web):August 26, 2015
DOI:10.1021/acs.orglett.5b01878
Catalyzed by [Rh(COD)Binapine]BF4, the asymmetric hydrogenation of 2-pyridine ketones has been achieved with excellent enantioselectivities (enantiomeric excesses up to 99%) under mild conditions. This method is suitable for various kinds of 2-pyridine ketones and their derivatives. A number of enantiomerically pure chiral 2-pyridine-aryl/alkyl alcohols were prepared through hydrogenation, which can be used directly in organic synthesis.
Co-reporter:Jianjian Ji, Caiyou Chen, Jiayu Cai, Xinrui Wang, Kai Zhang, Liyang Shi, Hui Lv and Xumu Zhang  
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 28) pp:7624-7627
Publication Date(Web):11 Jun 2015
DOI:10.1039/C5OB01111F
By employing a rhodium–Duanphos complex as the catalyst, β-alkyl (Z)-N-acetyldehydroamino esters were smoothly hydrogenated in a highly efficient and enantioselective way. Excellent enantioselectivities together with excellent yields were achieved for a series of substrates. An efficient approach for the synthesis of the intermediate of the orally administered anti-diabetic drugs Alogliptin and Linagliptin in the DPP-4 inhibitor class was also developed.
Co-reporter:Min Gao;Dr. Jing-jing Meng;Dr. Hui Lv;Dr. Xumu Zhang
Angewandte Chemie 2015 Volume 127( Issue 6) pp:1905-1907
Publication Date(Web):
DOI:10.1002/ange.201410213

Abstract

An efficient and highly regio- and enantioselective catalytic asymmetric hydrogenation of α,γ-dienamido esters to γ,δ-unsaturated amido esters has been achieved using Rh/TangPhos as the catalyst. A series of γ,δ-unsaturated amido acids were furnished in excellent yields with up to 99 % ee. This effective methodology was applied in the asymmetric synthesis of key intermediate of Ramipril, an ACE inhibitor.

Co-reporter:Min Gao;Dr. Jing-jing Meng;Dr. Hui Lv;Dr. Xumu Zhang
Angewandte Chemie International Edition 2015 Volume 54( Issue 6) pp:1885-1887
Publication Date(Web):
DOI:10.1002/anie.201410213

Abstract

An efficient and highly regio- and enantioselective catalytic asymmetric hydrogenation of α,γ-dienamido esters to γ,δ-unsaturated amido esters has been achieved using Rh/TangPhos as the catalyst. A series of γ,δ-unsaturated amido acids were furnished in excellent yields with up to 99 % ee. This effective methodology was applied in the asymmetric synthesis of key intermediate of Ramipril, an ACE inhibitor.

Co-reporter:Qingli Wang ; Wenhua Huang ; Haoquan Yuan ; Qin Cai ; Liming Chen ; Hui Lv ;Xumu Zhang
Journal of the American Chemical Society 2014 Volume 136(Issue 46) pp:16120-16123
Publication Date(Web):October 29, 2014
DOI:10.1021/ja509005e
Asymmetric hydrogenation of tetrasubtitued α-acetoxy β-enamido esters with rhodium catalysts based on chiral diphosphine ligands provides an efficient and concise route to the synthesis of chiral α-hydroxyl-β-amino acid derivatives in excellent enantioselectivities. The products are valuable chiral building blocks in many biologically active compounds and have important applications in organic synthesis.
Co-reporter:Ming Zhou, Tang-Lin Liu, Min Cao, Zejian Xue, Hui Lv, and Xumu Zhang
Organic Letters 2014 Volume 16(Issue 13) pp:3484-3487
Publication Date(Web):June 16, 2014
DOI:10.1021/ol501421g
Highly regioselective and enantioselective asymmetric hydrogenation of cyclic dienamides catalyzed by an Rh-DuanPhos complex has been developed, which provides a readily accessible method for the synthesis of chiral cyclic allylic amines in excellent enantioselectivities (up to 99% ee). The products are valuable chiral building blocks and could be easily transformed to multisubstituted cyclohexane derivatives.
Co-reporter:Xiuxiu Li, Cai You, Yusheng Yang, Fangyuan Wang, Shuailong Li, Hui Lv and Xumu Zhang
Chemical Communications 2017 - vol. 53(Issue 7) pp:NaN1316-1316
Publication Date(Web):2017/01/10
DOI:10.1039/C6CC09662J
An efficient rhodium-catalyzed asymmetric hydrogenation of α-amino acrylonitriles has been developed, affording α-acylamino nitriles with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). This novel methodology provides an efficient and concise synthetic route to chiral α-amino nitriles, which are versatile intermediates in organic synthesis.
Co-reporter:Yu-Qing Guan, Min Gao, Xu Deng, Hui Lv and Xumu Zhang
Chemical Communications 2017 - vol. 53(Issue 58) pp:NaN8139-8139
Publication Date(Web):2017/06/16
DOI:10.1039/C7CC03902F
A rhodium-catalyzed asymmetric hydrogenation of challenging tetrasubstituted β-acetoxy-α-enamido esters was developed, giving chiral β-acetoxy-α-amido esters in high yields with excellent enantioselectivities (up to >99% ee). The products could be easily transformed to β-hydroxy-α-amino acid derivatives which are valuable chiral building blocks and a novel route for the synthesis of droxidopa was also developed.
Co-reporter:Biao Wei, Caiyou Chen, Cai You, Hui Lv and Xumu Zhang
Inorganic Chemistry Frontiers 2017 - vol. 4(Issue 2) pp:NaN291-291
Publication Date(Web):2016/12/06
DOI:10.1039/C6QO00641H
A concise and efficient synthesis of (S,R)-Bn-Yanphos on a gram scale has been developed. When (S,R)-Bn-Yanphos was employed in Rh-catalyzed asymmetric hydroformylation of vinyl heteroarenes and allyl-1H-indole, it exhibited excellent catalytic activity, affording chiral heteroaryl aldehydes in good yields with high regio- and enantioselectivities (up to 96% ee).
Co-reporter:Xuefeng Tan, Qingli Wang, Yuanhua Liu, Fangyuan Wang, Hui Lv and Xumu Zhang
Chemical Communications 2015 - vol. 51(Issue 61) pp:NaN12196-12196
Publication Date(Web):2015/06/12
DOI:10.1039/C5CC04242A
A hydrazine group-containing nitrogen–phosphine ligand and corresponding ruthenium complexes were synthesized. When these complexes were used for hydrogenation of esters, excellent performance was observed (TON up to 17200). A wide substrate scope was suitable for this catalytic system.
Co-reporter:Jianjian Ji, Caiyou Chen, Jiayu Cai, Xinrui Wang, Kai Zhang, Liyang Shi, Hui Lv and Xumu Zhang
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 28) pp:NaN7627-7627
Publication Date(Web):2015/06/11
DOI:10.1039/C5OB01111F
By employing a rhodium–Duanphos complex as the catalyst, β-alkyl (Z)-N-acetyldehydroamino esters were smoothly hydrogenated in a highly efficient and enantioselective way. Excellent enantioselectivities together with excellent yields were achieved for a series of substrates. An efficient approach for the synthesis of the intermediate of the orally administered anti-diabetic drugs Alogliptin and Linagliptin in the DPP-4 inhibitor class was also developed.
BENZO[B]THIOPHENE-2-PROPANAL
1H-Indole-2-propanal, 1-[(4-methylphenyl)sulfonyl]-
Acetamide, N-(2-phenyl-1-cyclohexen-1-yl)-
(R)-Binapine
Cyclohexanone, 2-(1-methyl-1H-indol-2-yl)-
Benzoic acid, 4-(2-oxocyclohexyl)-, methyl ester
1H-Indole-1-propanal