Synthesis of. alpha.-hydroxy ketones by direct, low-temperature, in situ nucleophilic acylation of aldehydes and ketones by acyllithium reagents

D Seyferth, RM Weinstein, RC Hui…

Index: Seyferth, Dietmar; Weinstein, Robert M.; Hui, Richard C.; Wang, Wei-Liang; Archer, Colin M. Journal of Organic Chemistry, 1992 , vol. 57, # 21 p. 5620 - 5629

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Citation Number: 31

Abstract

The reaction of n-, see, and tert-butyllithium with CO at atmospheric pressure at-110 and- 135 OC in the appropriate solvent system in the presence of ketones and aldehydes generates the acyllithium, RC (O) Li, which rea& with the carbonyl compound to give the a- hydroxy ketone, generally in good yield. Reactions with aldehydes are limited in scope, working well with the t-BuLi-derived acyllithium reagents, but not with n-BuC (0) Li.