[4+2] Cycloaddition of Ketenes with N-Benzoyldiazenes Catalyzed by N-Heterocyclic Carbenes

被引：220

作者：

Huang, Xue-Liang ^{[1
]}

He, Lin ^{[1
]}

Shao, Pan-Lin ^{[1
]}

Ye, Song ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, Res Ctr Chem Biol, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 01期

关键词：

carbenes; cycloaddition; enantioselectivity; ketenes; synthetic methods; HIGHLY ENANTIOSELECTIVE SYNTHESIS; BAYLIS-HILLMAN REACTION; AZA-BETA-LACTAMS; ASYMMETRIC-SYNTHESIS; ORGANOCATALYSIS; ENONES;

D O I：

10.1002/anie.200804487

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Enantioselectivity switch: A catalytic enantioselective [4+2] cycloaddition reaction of alkylarylketenes with N-aryl-N′-benzoyldiazenes or N,N′-dibenzoyldiazenes to give 1,3,4-oxadiazin-6-ones 1 was developed by employing N-heterocyclic carbene (NHC) catalysts. The enantioselectivities could be switched for most reactions by changing the substituents on the NHC catalyst. TBS=tert-butyldimethylsilyl, Mes=2,4,6-trimethylphenyl. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：192 / 195

页数：4

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