Reaction of aldehydes and ketones with a boron-substituted carbanion, bis (ethylenedioxyboryl) methide. Simple aldehyde homologation

DS Matteson, RJ Moody, PK Jesthi

Index: Matteson,D.S. et al. Journal of the American Chemical Society, 1975 , vol. 97, # 19 p. 5608 - 5609

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Citation Number: 47

Abstract

Tris (ethylenedioxybory1) methane (1) with methyllithium yields lithium bis (ethylenedioxybory1) methide (2), which reacts with aldehydes or ketones to give high yields of alkeneboronic esters (3). Oxidation with buffered aqueous hydrogen peroxide'or alkaline sodium perborate results in a simple and efficient conversion of the carbonyl compound to the homologous aldehyde (4). An unexpected and potential-