Trimethylsilyldiazomethane in the preparation of diazoketones via mixed anhydride and coupling reagent methods: a new approach to the Arndt-Eistert synthesis

被引：33

作者：

Cesar, J ^{[1
]}

Dolenc, MS ^{[1
]}

机构：

[1] Univ Ljubljana, Fac Pharm, Ljubljana 1000, Slovenia

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 40期

关键词：

trimethylsilyldiazomethane; Arendt-Eistert synthesis; mixed anhydrides; diazoketones; Wolff rearrangement; dicyclohexylcarbodiimide; N-hydroxysuccinimide;

D O I：

10.1016/S0040-4039(01)01458-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction or trimethylsilyldiazomethane with a mixed anhydride derived from a carboxylic acid by the action of ethyl chloroformate, yields the corresponding diazoketone in high yield, Subsequent Wolff rearrangement of the diazoketone leads to the homologated ester. Reaction of trimethylsilyldiazomethane with carboxylic acid-dicyclohexylcarbodiimide mixtures leads to the formation of diazoketone and trimethylsilylmethyl ester in equimolar ratio via an acid anhydride intermediate. The N-hydroxysuccinimide ester of the acid does not react with trimethylsilyldiazomethane or with its more reactive lithiated derivative. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：7099 / 7102

页数：4

共 24 条

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[2] NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .8. TRIMETHYLSILYLDIAZOMETHANE, A NEW, STABLE, AND SAFE REAGENT FOR THE CLASSICAL ARNDT-EISTERT SYNTHESIS [J].