Organocatalytic Asymmetric Inverse-Electron-Demand Aza-Diels-Alder Reaction of N-Sulfonyl-1-aza-1,3-butadienes and Aldehydes

被引：165

作者：

Han, Bo ^{[1
]}

Li, Jun-Long ^{[1
]}

Ma, Chao ^{[1
]}

Zhang, Shan-Jun ^{[1
]}

Chen, Ying-Chun ^{[1
,2
]}

机构：

[1] Sichuan Univ, W China Sch Pharm, Dept Med Chem, Minist Educ,Key Lab Drug Targeting & Drug Deliver, Chengdu 610041, Peoples R China

[2] Sichuan Univ, W China Hosp, State Key Lab Biotherapy, Chengdu 610041, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 51期

关键词：

aldehydes; aminocatalysis; asymmetric catalysis; aza-Diels-Alder reaction; piperidines;

D O I：

10.1002/anie.200804183

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Water is crucial for high transformation efficiency in the title reaction catalyzed by the α,α- diphenylprolinol derivative 1. Excellent stereoselectivities were observed for a broad spectrum of substrates (see scheme; TMS = trimethylsilyl, Tos = p-toluenesulfonyl). A diverse range of chiral piperidine derivatives and other valuable compounds can be prepared from the hemiaminal products. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：9971 / 9974

页数：4

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