Enantioselective Organocatalytic Conjugate Addition of Aldehydes to α,β-Unsaturated Thiol Esters

被引：24

作者：

Zhu, Shaolin ^{[1
]}

Wang, You ^{[2
]}

Ma, Dawei ^{[1
]}

机构：

[1] Chinese Acad Sci, State Key Lab Bioorgan & Nat Prod Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

[2] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 16期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; enamine activation; Michael addition; organocatalysis; alpha; beta-unsaturated thiol esters; DIPHENYLPROLINOL SILYL ETHER; ASYMMETRIC MICHAEL REACTIONS; VINYL SULFONES; GAMMA(2)-AMINO ACIDS; 4; STEREOCENTERS; CHIRAL AMINES; WATER; NITROETHYLENE; NITROOLEFINS; NITROALKENES;

D O I：

10.1002/adsc.200900449

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The first example of an organocatalytic asymmetric Michael addition of aldehydes to alpha,beta-unsaturated thiol esters promoted by chiral diphenylprolinol silyl ether is presented. The reaction occurs with good yields, diastereoselectivity and excellent enantioselectivity.

引用

页码：2563 / 2566

页数：4

共 50 条

[41] Organocatalytic enantioselective conjugate addition of ketones to isatylidine malononitriles
Liu, Lu
Wu, Deyan
Li, Xiangmin
Wang, Sinan
Li, Hao
Li, Jian
Wang, Wei
CHEMICAL COMMUNICATIONS, 2012, 48 (11) : 1692 - 1694
[42] Organocatalytic Enantioselective Conjugate Addition of 3-Fluorooxindoles to Vinyl Sulfone
Kim, Yi Seul
Kwon, Su Jin
Kim, Dae Young
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (05): : 1512 - 1515
[43] Diastereo- and Enantioselective Organocatalytic Direct Conjugate Addition of γ-Butenolide to Chalcones
Zhang, Yinan
Yu, Chenguang
Ji, Yafei
Wang, Wei
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (06) : 1303 - 1306
[44] Enantioselective Organocatalytic Michael Addition of Malonates to α,β-Unsaturated Ketones
Li, Pengfei
Wen, Shigang
Yu, Feng
Liu, Qiaoxia
Li, Wenjun
Wang, Yongcan
Liang, Xinmiao
Ye, Jinxing
ORGANIC LETTERS, 2009, 11 (03) : 753 - 756
[45] Organocatalytic Michael Addition of Nitro Esters to α,β-Unsaturated Aldehydes: Towards the Enantioselective Synthesis of trans-3-Substituted Proline Derivatives
Han, Man-Yi
Zhang, Yong
Wang, Huai-Zhen
An, Wan-Kai
Ma, Bao-Chun
Zhang, Yuan
Wang, Wei
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (14-15) : 2635 - 2640
[46] Organocatalytic Asymmetric Michael Addition of 1,3-Cyclohexanedione to β,γ-Unsaturated α-Keto Esters
Lee, Hyun Joo
Kim, Dae Young
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (11): : 3537 - 3538
[47] Organocatalytic Enantioselective Michael Addition of Silyl Malonate to α,β-Unsaturated Enones: One-pot Synthesis of Chiral δ-Keto Esters
Lee, Ji Yeon
Kim, Dae Young
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (09): : 2569 - 2570
[48] The Organocatalytic Enantioselective Michael Addition of Aldehydes to Vinyl Sulfones in Water
Xiao, Jian
Liu, Yan-Ling
Loh, Teck-Peng
SYNLETT, 2010, (13) : 2029 - 2032
[49] Asymmetric Construction of Benzindoloquinolizidine: Application of An Organocatalytic Enantioselective Conjugate Addition-Cyclization Cascade Reaction
Kim, Cheolwoong
Seo, Seung Woo
Lee, Yona
Kim, Sung-Gon
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2014, 35 (02): : 625 - 628
[50] Highly Enantioselective Conjugate Additions of Aldehydes to Vinyl Sulfones
Landa, Aitor
Maestro, Miguel
Masdeu, Carme
Puente, Angel
Vera, Silvia
Oiarbide, Mikel
Palomo, Claudio
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (07) : 1562 - 1565

← 1 2 3 4 5 →