期刊
TETRAHEDRON LETTERS
卷 42, 期 40, 页码 7099-7102出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(01)01458-7
关键词
trimethylsilyldiazomethane; Arendt-Eistert synthesis; mixed anhydrides; diazoketones; Wolff rearrangement; dicyclohexylcarbodiimide; N-hydroxysuccinimide
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.
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