Enzymatic synthesis of chiral 1-phenyl-1,2- and 1,3-diols via chiral epoxy alcohols

Abstract

Chiral epoxy alcohols have been prepared by asymmetric reduction of 1-phenyl-2,3-epoxybutan-1-one with baker's yeast, or by enantioselective esterification of racemic 1-phenyl-2,3-epoxybutan-1-ol with lipase PS. The epoxy alcohols obtained were reduced with lithium aluminium hydride to afford chiral 1-phenylbutane-1,2- and 1,3-diols. The absolute configurations of the epoxy alcohols and diols were determined by use of modified Mosher's method or by the comparison with the diols, which were prepared from benzoylacetone via chiral enols by use of baker's yeast and lipase PS.