THE PRODUCT OF BAKER'S YEAST REDUCTION OF ETHYL 2-CHLORO-3-OXOBUTANOATE AS A PRECURSOR OF THE 1-ETHOXYCARBONYL 2(S)-HYDROXYPROPYL RADICAL

Article abstract of DOI:10.1016/S0957-4166(00)80233-5

Baker's yeast treatment of ethyl 2-chloro-3-oxobutanoate 1, diethyl 2-acetylmalonate 2 and ethyl 2-cyano-3-oxobutanoate 3 was effected in order to obtain enantiomerically enriched compounds.In contrast to the reaction of 2 and 3, efficient diastereo- and enantioselective reduction of 1 provided ethyl 2(R)-chloro-3(S)-hydroxybutanoate.This product was used as precursor of the 1-ethoxycarbonyl-2(S)-hydroxypropyl radical and the diastereoselectivity of the addition of this intermediate to alkenes was studied.