Synthesis of α-nitro-α-diazocarbonyl derivatives and their applications in the cyclopropanation of alkenes and in O-H insertion reactions

被引：58

作者：

Charette, AB ^{[1
]}

Wurz, RP ^{[1
]}

Ollevier, T ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada

来源：

HELVETICA CHIMICA ACTA | 2002年 / 85卷 / 12期

关键词：

D O I：

10.1002/hlca.200290023

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile and highly efficient method for the preparation of alpha-nitro-alpha-diazocarbonyl derivatives by a diazo-transfer reaction involving (trifluoromethyl)sulfonyl azide has been developed. These substrates undergo a rhodium-catalyzed cyclopropanation reaction with a variety of alkenes. A systematic study of the reaction indicated that the diastereoselectivity of the cyclopropanation could be effectively controlled through the modification of the steric hulk of the diazo reagent. A novel O - H insertion reaction of the metal - carbene complex derived from the alpha-nitro-alpha-diazocarbonyl reagent afforded the corresponding, novel alpha-nitro-alpha-alkoxy carbonyl derivatives.

引用

页码：4468 / 4484

页数：17

共 64 条

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