N-Heterocyclic Carbene Catalysis: Enantioselective Formal [2+2] Cycloaddition of Ketenes and N-Sulfinylanilines

被引：98

作者：

Jian, Teng-Yue ^{[1
]}

He, Lin ^{[1
]}

Tang, Cen ^{[1
]}

Ye, Song ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 39期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; cycloaddition; ketenes; N-heterocyclic carbene; sultams; SULFUR-DIOXIDE; ELASTASE; 3-OXO-BETA-SULTAMS; ORGANOCATALYSIS; DERIVATIVES; INHIBITION; HYDROLYSIS; 1-OXIDES; LACTONES; AMINES;

D O I：

10.1002/anie.201102488

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Sultam of swing: Both enantiomers of 1,2-thiazetidin-3-one oxides were obtained in very good yields with excellent enantioselectivities when using N-heterocyclic carbene catalysts (see scheme; M.S.=molecular sieves, TBS=tert-butyldimethylsilyl). The products were easily converted into 3-oxo-β-sultams, α-mercapto amides, and β-mercapto amines through oxidation or reduction. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9104 / 9107

页数：4

共 41 条

[1] Partial protection against botulinum B neurotoxin-induced blocking of exocytosis by a potent inhibitor of its metallopeptidase activity [J].