Baker's yeast mediated reduction of dihydroxyacetone derivatives

Abstract

Several monoprotected dihydroxyacetone derivatives 4a– d and their acetates 5a– d were prepared and subjected to biotransformation with baker's yeast. The simple chemical modification of the substrates (i.e. transforming the relatively small hydrophilic hydroxymethyl group into a larger hydrophobic acetoxymethyl moiety) inverted the sense of enantiotope selectivity of these reductions yielding optically active diols 6a– d, or their enantiomeric acetates ( 7a– d) and diols ( ent- 6a– d), respectively.