Asymmetric synthesis of highly functionalized γ-lactams through an organocatalytic aza-Michael-Michael reaction cascade using fumaric acid amide esters as multi-reactive substrates

被引：20

作者：

Yokosaka, Takuya ^{[1
]}

Hamajima, Akinari ^{[1
]}

Nemoto, Tetsuhiro ^{[1
]}

Hamada, Yasumasa ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, Chiba 2608675, Japan

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 10期

关键词：

Asymmetric synthesis; Cascade catalysis; Lactam; Organocatalyst; Michael reaction; DIPHENYLPROLINOL SILYL ETHER; ONE-POT SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; ORGANOCASCADE CATALYSIS; ENANTIOSELECTIVE SYNTHESIS; DOMINO REACTIONS; STEREOCENTERS; EFFICIENT; CONSTRUCTION; DERIVATIVES;

D O I：

10.1016/j.tetlet.2011.12.114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed a novel method for the asymmetric synthesis of highly functionalized gamma-lactams through an organocatalytic aza-Michael-Michael reaction cascade using fumaric acid amide esters as multi-reactive substrates. Using chiral primary or secondary amine organocatalysts, we obtained two types of gamma-lactams with three contiguous chiral centers in moderate to good yield with excellent enantioselectivity and diastereoselectivity. (C) 2012 Published by Elsevier Ltd.

引用

页码：1245 / 1248

页数：4

共 21 条

[1] Organocatalytic Enantioselective Cascade Aza-Michael/Michael Addition for the Synthesis of Highly Functionalized Tetrahydroquinolines and Tetrahydrochromanoquinolines
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[5] Organocatalytic Aza-Michael/Mannich Cascade Reaction: Synthesis of Enantioenriched 3,3′-Spirooxindole γ-Lactams
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