Efficient aziridination of olefins catalyzed by mixed-valent dirhodium(II,III) caprolactamate

被引：102

作者：

Catino, AJ ^{[1
]}

Nichols, JM ^{[1
]}

Forslund, RE ^{[1
]}

Doyle, MP ^{[1
]}

机构：

[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 13期

关键词：

D O I：

10.1021/ol0510973

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild, efficient, and selective aziridination of olefins catalyzed by dirhodium(II) caprolactamate [Rh-2(cap)(4)center dot 2CH(3)CN] is described. Use of p-toluenesulfonamide (TsNH2), N-bromosuccinimide (NBS), and potassium carbonate readily affords aziridines in isolated yields of up to 95% under extremely mild conditions with as little as 0.01 mol% Rh-2(cap)(4). Aziridine formation occurs through Rh-2(5+)-catalyzed aminobromination and subsequent base-induced ring closure. An X-ray crystal structure of a Rh-2(5+) halide complex, formed from the reaction between Rh-2(cap)(4) and N-chlorosuccinimide, has been obtained.

引用

页码：2787 / 2790

页数：4

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