Eighteen known and putative reductases from baker's yeast(Saccharomycescerevisiae) were tested for the ability toreduce a series of α-chloro-β-keto esters. In nearly all cases,it was possible to produce at least two of the four possibleα-chloro-β-hydroxy ester diastereomers with high opticalpurities. The utility of this approach was demonstrated byreducing ethyl 2-chloroacetoacetate to the corresponding syn-(2R,3S)-alcohol on a multigram scale using whole cells ofan Escherichiacoli strain overexpressing a single yeastreductase identified from the screening studies.