Bifunctional Phosphine-Catalyzed Domino Reaction: Highly Stereoselective Synthesis of cis-2,3-Dihydrobenzofurans from Salicyl N-Thiophosphinyl Imines and Allenes

被引：113

作者：

Meng, Xiangtai

Huang, You ^{[1
]}

Chen, Ruyu

机构：

[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 01期

基金：

中国国家自然科学基金;

关键词：

BAYLIS-HILLMAN REACTION; MICHAEL-ALDOL REACTIONS; ASYMMETRIC ORGANOCATALYTIC SYNTHESIS; ENANTIOSELECTIVE 3+2 ANNULATIONS; DIELS-ALDER REACTION; METHYL VINYL KETONE; ONE-POT SYNTHESIS; C-H INSERTION; BRONSTED ACID; SULFONATED IMINES;

D O I：

10.1021/ol802453c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new bifunctional phosphine catalyst, (2'-hydroxy-biphenyl-2-yl)-diethylphosphane (LBBA-1), was developed for the highly stereoselective synthesis of cis-2,3-dihydrobenzofurans via an aza-Morita-Baylis-Hillman/umpolung addition domino reaction of salicyl N-thiophosphinyl Imines with electron-deficient allenes. Dual activation of both nucleophile and electrophile by the bifunctional catalyst accounts for the observed high reactivity and stereoselectivity.

引用

收藏

页码：137 / 140

页数：4

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