Highly Enantioselective Aza-Diels-Alder Reaction of 1-Azadienes with Enecarbamates Catalyzed by Chiral Phosphoric Acids

被引：80

作者：

He, Long ^{[1
]}

Laurent, Gregory ^{[1
]}

Retailleau, Pascal ^{[1
]}

Folleas, Benoit ^{[2
]}

Brayer, Jean-Louis ^{[2
]}

Masson, Geraldine ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France

[2] ZAC Moulin, Diverchim, F-95700 Roissy En France, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 42期

关键词：

cycloaddition; dienes; heterocycles; organocatalysis; synthetic methods; BRONSTED ACID; POVAROV REACTION; GLYCOSIDASE INHIBITORS; 4-PI PARTICIPATION; ROOM-TEMPERATURE; ACTIVATION; 1-AZA-1,3-BUTADIENES; ALDEHYDES; ENAMIDES; ACCESS;

D O I：

10.1002/anie.201304969

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

On demand: A highly enantio- and diastereoselective synthesis of 6-amino- trisubstituted tetrahydropyridine compounds has been developed through the inverse-electron-demand aza-Diels-Alder reaction of N-aryl α,β- unsaturated ketimines with enecarbamates (E)-1. Chiral phosphoric acid catalysts achieve simultaneous activation of both the 1-azadiene and dienophile partners. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：11088 / 11091

页数：4

共 102 条

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