Primary allenic alcohols of high optical purity via lipase catalyzed resolution

Abstract

The lipase from Candida rugosa lipase (CRL) was used for the preparation of optically active primary allenic alcohols with axial chirality. The biocatalytic material used was the commercial CRL (C-CRL) and propan-2-ol-treated CRL (PT-CRL). The kinetic resolution of (±)- 1 and (±)- 3a– c in water using C-CRL resulted in either the absence of or low enantiomeric ratio, whereas PT-CRL increased the E-value. Under optimized conditions (temperature and medium used) (+)- S- 3a and (−)- R- 4 were isolated in excellent yields and high optical purity (o.p.). The resolution was carried out on multigram scale in water/ n-hexane at 4 °C.