Organocatalytic Regio- and Stereoselective Inverse-Electron-Demand Aza-Diels-Alder Reaction of α,β-Unsaturated Aldehydes and N-Tosyl-1-aza-1,3-butadienes

被引：190

作者：

Han, Bo ^{[1
]}

He, Zhao-Quan ^{[1
]}

Li, Jun-Long ^{[1
]}

Li, Rui ^{[2
]}

Jiang, Kun ^{[1
]}

Liu, Tian-Yu ^{[1
]}

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

机构：

[1] Sichuan Univ, W China Sch Pharm, Dept Med Chem, Key Lab Drug Targeting & Drug Delivery Syst Educ, 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 | 2009年 / 48卷 / 30期

关键词：

asymmetric catalysis; aza-Diels-Alder reaction; dienamine catalysis; piperidines; alpha; beta-unsaturated aldehydes; DIPHENYLPROLINOL SILYL ETHER; ASYMMETRIC MICHAEL REACTION; 4-PI PARTICIPATION; 3+3 CYCLOADDITION; CATALYSIS; CASCADE; ACIDS; N-SULFONYL-1-AZA-1,3-BUTADIENES; 1-AZA-1,3-BUTADIENES; AMINOCATALYSIS;

D O I：

10.1002/anie.200902216

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dienamines formed in situ from a chiral secondary amine and an α, β-unsaturated aldehyde undergo the highly α- regioselective title reaction to give densely functionalized piperidine derivatives with excellent enantioselectivity (see scheme). The products were converted into a variety of versatile cyclic frameworks. Ts=4-toluenesulfonyl. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5474 / 5477

页数：4

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