Asymmetric conjugate addition of carbonyl compounds to nitroalkenes catalyzed by chiral bifunctional thioureas

被引：65

作者：

Zhang, Xue-jing ^{[1
]}

Liu, Sheng-ping ^{[1
]}

Lao, Jin-hua ^{[1
]}

Du, Guang-jian ^{[1
]}

Yan, Ming ^{[1
]}

Chan, Albert S. C. ^{[1
,2
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Ind Inst Fine Chem & Synth Drugs, Guangzhou 510006, Guangdong, Peoples R China

[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 12期

基金：

中国国家自然科学基金;

关键词：

ORGANOCATALYTIC MICHAEL ADDITION; ALDOL REACTIONS; GAMMA(2)-AMINO ACIDS; ENAMINE CATALYSIS; RATIONAL APPROACH; AMINE CATALYSTS; SYN-ALDOL; ALDEHYDES; KETONES; WATER;

D O I：

10.1016/j.tetasy.2009.06.003

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Readily available chiral thioureas derived from cyclohexane-1,2-diamine were prepared and found to be highly effective organocatalysts for the Conjugate addition of aldehydes and ketones to nitroalkenes. Excellent enantioselectivities and yields were obtained for a variety of aryl and heteroaryl nitroalkenes. The base additives are essential for good yields and excellent enantioselectivities in this transformation. Based oil new experimental evidence, a modified catalytic mechanism was proposed to rationalize the important role of the base additives. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1451 / 1458

页数：8

共 50 条

[1] Asymmetric conjugate addition of ketones to nitroalkenes catalyzed by chiral bifunctional sulfamides
Liu, Sheng-ping
Zhang, Xue-jing
Lao, Jin-hua
Yan, Ming
ARKIVOC, 2009, : 268 - 280
[2] Rencent Advances in Asymmetric Michael Addition Catalyzed by Chiral Bifunctional Thioureas
Hou, Xuehui
Ma, Zhiwei
Wang, Jianling
Liu, Hongmin
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (08) : 1509 - 1522
[3] Palladium-catalyzed conjugate addition of organosiloxanes to α,β-unsaturated carbonyl compounds and nitroalkenes
Denmark, SE
Amishiro, N
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18): : 6997 - 7003
[4] Asymmetric Crossed-Conjugate Addition of Nitroalkenes to Enones by a Chiral Bifunctional Diamine Organocatalyst
Wang, Min
Lin, Lili
Shi, Jian
Liu, Xiaohua
Kuang, Yulong
Feng, Xiaoming
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (08) : 2365 - 2368
[5] Asymmetric Michael/cyclization tandem reaction of 4-hydroxycoumarin with β-nitroalkenes catalyzed by chiral bifunctional thioureas
Mei, Ren-Qiang
Xu, Xiao-Ying
Peng, Lin
Wang, Fan
Tian, Fang
Wang, Li-Xin
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (08) : 1286 - 1289
[6] Chiral amidophosphane-copper-catalyzed asymmetric conjugate addition of dialkylzinc reagents to nitroalkenes
Valleix, F
Nagai, K
Soeta, T
Kuriyama, M
Yamada, K
Tomioka, K
TETRAHEDRON, 2005, 61 (31) : 7420 - 7424
[7] Asymmetric Michael addition of arylthiols to α,β-unsaturated carbonyl compounds catalyzed by bifunctional organocatalysts
Li, BJ
Jiang, L
Liu, M
Chen, YC
Ding, LS
Wu, Y
SYNLETT, 2005, (04) : 603 - 606
[8] Asymmetric conjugate addition of azide to α,β-unsaturated carbonyl compounds catalyzed by simple peptides
Horstmann, TE
Guerin, DJ
Miller, SJ
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (20) : 3635 - 3638
[9] Michael Addition of Thiols to á, -Unsaturated Carbonyl Compounds Catalyzed by Bifunctional Organocatalysts: Asymmetric Michael Addition and Asymmetric Protonation
LI BangJing JIANG Lin LIU Min DING LiSheng CHEN YingChun West China School of Pharmacy Sichuan University Chengdu China Chengdu Institute of Biology Chinese Academy of Sciences Chengdu China
合成化学, 2004, (S1) : 48 - 48
[10] Asymmetric Conjugate Addition of 1,3-Diketone to Nitroalkenes Catalyzed by Bifunctional Thiourea-Amide Organocatalysts
Bai, Bing
Wang, Long
Yang, Jing
Cai, Lili
Liu, Qianjin
Xi, Gaolei
Zhao, Zhiwei
Mao, Duobin
Chen, Zhifei
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (04) : 1053 - 1063

← 1 2 3 4 5 →