Phosphine-Promoted [3+3] Annulations of Aziridines With Allenoates: Facile Entry Into Highly Functionalized Tetrahydropyridines

被引：192

作者：

Guo, Hongchao ^{[1
]}

Xu, Qihai ^{[1
]}

Kwon, Ohyun ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 18期

关键词：

ELECTRON-DEFICIENT OLEFINS; NATURAL-PRODUCT SYNTHESIS; CATALYZED 4+2 ANNULATION; DIPOLAR CYCLOADDITION; NITRONES; IMINES; 2,3-BUTADIENOATES; CYCLOPROPANES; DERIVATIVES;

D O I：

10.1021/ja8097349

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The phosphine-mediated [3 + 3] annulations of aziridines and allenes are experimentally simple reactions, run under very mild conditions, for the preparation of highly functionalized tetrahydropyridines in yields of up to 98% and trans/cis ratios of up to 97:3. In addition to steps that are typical of nucleophilic phosphine-catalyzed reactions of allenoates, the mechanism of this new reaction features apparent nucleophilic aromatic substitution and concomitant desulfonylation, processes hitherto unknown during phosphine-promoted cycloaddition reactions. Notably, these reactions are the first reported examples of aziridines as reaction partners in nucleophilic phosphine-catalyzed transformations.

引用

页码：6318 / +

页数：3

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