Stereospecific Ring Expansion of Chiral Vinyl Aziridines

被引：56

作者：

Brichacek, Matthew ^{[1
]}

Villalobos, Mauricio Navarro ^{[1
]}

Plichta, Alexandra ^{[1
]}

Njardarson, Jon T. ^{[1
,2
]}

机构：

[1] Cornell Univ, Baker Lab, Dept Chem & Chem Biol, Ithaca, NY 14853 USA

[2] Univ Arizona, Dept Chem & Biochem, Tucson, AZ 85721 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 05期

关键词：

ASYMMETRIC-SYNTHESIS; AMINO-ACIDS; PYRROLIZIDINE ALKALOIDS; AMINOSULFOXONIUM SALTS; PROLINE ANALOGS; REARRANGEMENT; VINYLAZIRIDINES; STEREOCHEMISTRY; TRANSFORMATION; SULFINIMINES;

D O I：

10.1021/ol200263g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this report, it is demonstrated that chiral vinyl aziridines can be stereospecifically ring expanded. This synthetic approach allows controlled access to chiral 2,5-cis- or 2,5-trans-3-pyrroline products from starting materials with the appropriate aziridine geometry. Twenty three ring expansion examples, most of which feature a stereospecific cyclization, are presented.

引用

页码：1110 / 1113

页数：4

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