Enzymatic preparation and absolute configuration of (+)-2-(hydroxymethyl)cyclohexanone

Abstract

Lipase mediated treatment of racemic 2-(hydroxymethyl)cyclohexanone, (+/-)-1, with vinyl acetate allows enantioselective acetylation to give the acetate (R)-(+)-4 and unreacted (S)-(+)-1 in satisfactory yield and enantiomeric purity. The absolute configuration of (S)-(+)-1 (and therefore that of (R)-(+)-4 as well) was determined by the analysis of the n-->pi* Cotton effect at 290 nm present in the CD spectrum of (S)-(+)-1 by means of the octant rule and CNDO/S calculations. Furthermore the optical rotatory power of optically pure (S)-(+)-1 and (R)-(+)-4 have been determined