Tetrahedron Letters

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

J Cesar, MS Dolenc

文献索引：Cesar, Jozko; Sollner Dolenc, Marija Tetrahedron Letters, 2001 , vol. 42, # 40 p. 7099 - 7102

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被引用次数: 40

摘要

Reaction of 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 ...