Asymmetric 1,3-dipolar cycloadditions of a chiral nonracemic glyoxylic azomethine imine

被引：28

作者：

Chung, F

Chauveau, A

Seltki, M

Bonin, M

Micouin, L

机构：

[1] CNRS, UMR 8638, Chim Therapeut Lab, F-75270 Paris 06, France

[2] Univ Paris 05, Fac Sci Pharmaceut & Biol, F-75270 Paris 06, France

[3] CNRS, UMR 8015, Lab Cristallog, Fac Sic Pharmaceut & Biol, F-75270 Paris 06, France

[4] CNRS, UMR 8015, RMN Biol, Fac Sic Pharmaceut & Biol, F-75270 Paris 06, France

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 15期

关键词：

cycloadditions; azomethine imine; asymmetric synthesis;

D O I：

10.1016/j.tetlet.2004.02.088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactivity of a chiral nonracemic glyoxylic azomethine imine has been investigated. This species reacts with a wide range of dipolarophiles, with a complete regio- and facial stereoselectivity. The introduction of an electron-withdrawing substituent on the ylide leads to a lower endo selectivity with electron-withdrawing dipolarophiles, but to an improved exo selectivity with styrene derivatives when compared to the reactivity of aliphatic- or aromatic-substituted ylides. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3127 / 3130

页数：4

共 13 条

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