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

The reaction of n-, sec-, and tert-butyllithium with CO at atmospheric pressure at -110 and -135 o C in the appropriate solvent system in the presence of ketones and aldehydes generates the acyllithium, RC(O)Li, which reacts with the carbonyl compound to give the α-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(O)Li