Carbonyl Homologation via β-Trimethylsilyl β-Lactone Rearrangements. A Nonbasic Alternative to the Wittig Reaction

…, Y Zhang, J Huang, DC Smith, BE Yates

Index: Black; Zhang; Huang; Smith; Yates Synthetic Communications, 1995 , vol. 25, # 1 p. 15 - 20

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Citation Number: 15

Abstract

Abstract Saturated and unsaturated aldehydes and ketones, when treated with trimethylsilylketene and BF3 for 16 hours, form β-lactones which spontaneously rearrange to α, β-unsaturated TMS esters; these hydrolyze during workup to form the corresponding carboxylic acids.