Enantioselective aza-Diels-Alder reaction of Brassard's diene with aldimines catalyzed by chiral N,N′-dioxide-Yb(OTf)3 complex

被引：26

作者：

Chen, Zhenling ^{[1
]}

Lin, Lili ^{[1
]}

Chen, Donghui ^{[1
]}

Li, Jiangting ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 23期

基金：

中国国家自然科学基金;

关键词：

Brassard's diene; Aza-Diels-Alder reaction; Ytterbium; N; '-Dioxide; ALPHA-ALKOXY ALDEHYDES; ONE-STEP SYNTHESIS; LEWIS-ACID; ASYMMETRIC-SYNTHESIS; ACTIVATED DIENES; BRONSTED ACID; AMINO; EFFICIENT; DERIVATIVES; CHELATION;

D O I：

10.1016/j.tetlet.2010.04.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral N,N'-dioxide-Yb(OTf)(3) complex-catalyzed enantioselective aza-Diels-Alder reaction of Brassard's diene with aldimines has been developed, giving the corresponding alpha,beta-unsaturated delta-lactam derivatives in moderate yields with good enantioselectivities (up to 81% ee and up to 99% ee by single recrystallization) under mild conditions. Isolation of the reaction intermediate indicates that this asymmetric aza-Diels-Alder reaction proceeds through a stepwise Mannich-type pathway. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3088 / 3091

页数：4

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