YEAST REDUCTION OF SOME 4-CARBON CHLORINATED KETONES - A CONVENIENT SYNTHESIS OF (S)-(+)-BUT-3-EN-2-OL

The action of fermenting yeast on various four-carbon chlorinated ketones has been studied. (S)-(+)-But-3-en-2-ol is conveniently prepared from (+/-)-3-chlorobutan-2-one which yields a 1:1 mixture of (2S,3S)-and (2S,3R)-3-chlorobutan-2-ols. Conversion of the mixture into the dimethylmethoxymethyl ethers followed by dehydrohalogenation and hydrolysis then gives (S)-(+)-but-3-en-2-ol.