Yeast reduction of some four-carbon chlorinated ketones. A convenient synthesis of (S)-(+)-but-3-en-2-ol

Abstract

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 dimethyl-methoxymethyl ethers followed by dehydrohalogenation and hydrolysis then gives (S)-(+)-but-3-en-2-ol.