Chemocontrolled reduction of α-keto esters by hydrides: A possible solution for selective reduction of the ester function

Article abstract of DOI:10.1016/S0040-4020(99)00317-8

α-keto primary alcohols or α-silyloxy ketones have been obtained with a high level of selectivity from enolic α-keto esters in two steps, with the reduction of the α-silyloxy α,β-unsaturated ester by LiAlH₄ as the key step. The methodology developed in this work represents a 'reversed' chemoselective reduction of the ester group instead of the keto of an enolic α-keto ester due to a one-pot sequential ester reduction-desilylation or silyl migration process.