The Enantioface-differentiating Hydrogenation of the C=O Double Bond with Asymmetrically Modified Raney Nickel. XXXIII. The Preparation of (R)- and (S)-1,3-Butanediol from 4-Hydroxy-2-butanone

Abstract The enantioface-differentiating hydrogenation of 4-hydroxy-2-butanone (I) to 1,3-butanediol(II) was conducted with asymmetrically modified metal catalysts. Among the modified catalysts examined, Raney nickel modified with a solution containing tartaric acid and NaBr (TA–NaBr–MRNi) gave the best results with respect to the optical and chemical yields. (R)-II, an optical purity of 69% was obtained in a quantitative chemical yield by the use of (R,R)-TA–NaBr–MRNi. (S)-II was also obtained by the use of (S,S)-TA–NaBr–MRNi. A simple method for the preparation of optically pure (S)-and (R)-II from the hydrogenation product was also developed.