Preparation of Optically Pure (3<i>S</i>,5<i>S</i>)- and (3<i>R</i>,5<i>R</i>)-2,6-Dimethyl-3,5-heptanediol

Abstract

Abstract Optically pure 2,6-dimethyl-3,5-heptanediol (1), a new chiral auxiliary, has been prepared by the enantiodifferentiating hydrogenation of 2,6-dimethyl-3,5-heptanedione over tartaric acid–NaBr–modified Raney nickel catalyst (TA–NaBr–MRNi), and the preferential recrystallization of the hydrogenation product. Absolute configuration of 1 was determined to be 3S, 5S by the chemical correlation with (−)-ethyl (S)-3-hydroxy-4-methylpentanoate.