Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3+2] cycloadditions

被引：356

作者：

Fang, Yuan-Qing ^{[1
]}

Jacobsen, Eric N. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 17期

关键词：

D O I：

10.1021/ja801344w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new family of phosphinthiourea catalysts was developed for the highly enantioselective synthesis of 2-aryl-2,5-hydropyrroles via a [3 + 2] cycloaddition of an electron-deficient allene with aryl and heteroaryl diphenylphosphinoylimines. The presence of both H(2)O and Et(3)N as additives was found to be important for achieving optimal rates. Dual activation of both nucleophile and electrophile by the bifunctional catalyst is invoked to account for the observed high reactivity and enantioselectivity.

引用

页码：5660 / +

页数：3

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