Interplay of Direct Stereocontrol and Dynamic Kinetic Resolution in a Bifunctional Amine Thiourea Catalyzed Highly Enantioselective Cascade Michael-Michael Reaction

被引：65

作者：

Yu, Chenguang ^{[1
,2
]}

Zhang, Yinan ^{[1
]}

Song, Aiguo ^{[1
]}

Ji, Yafei ^{[1
,3
]}

Wang, Wei ^{[1
,3
,4
]}

机构：

[1] Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

[2] Beijing Univ Chem Technol, State Key Lab Chem Resources Engn, Beijing 100029, Peoples R China

[3] E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China

[4] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 03期

基金：

美国国家科学基金会;

关键词：

amine thioureas; cascade catalysis; dynamic kinetic resolution; organocatalysis; tetrahydrothiophenes; ASYMMETRIC TOTAL-SYNTHESIS; ORGANOCATALYTIC DOMINO REACTIONS; DIELS-ALDER REACTION; CONJUGATE ADDITION; CINCHONA ALKALOIDS; NONADJACENT STEREOCENTERS; ALDOL REACTIONS; BETA-KETOESTER; ACID; NITROOLEFINS;

D O I：

10.1002/chem.201002384

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Control is better: A novel chiral amine thiourea catalyzed, highly enantioselective Michael-Michael cascade process serves as a "one-pot" approach to synthetically and biologically significant chiral tetrahydrothiophenes (see scheme). Notably, an unprecedented cooperative direct stereocontrol and dynamic kinetic resolution by the bifunctional catalyst is identified that governs the highly enantioselective cascade process. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：770 / 774

页数：5

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