Enzymatic preparation of enantiomerically pure alkan-2- and -3-ols by lipase-catalysed hydrolysis with Pseudomonas cepacia in the presence of organic media

Abstract

Pseudomonas cepacia lipase-catalysed hydrolysis of the acetates of racemic alkan-2- and -3-ols was carried out in the presence of organic media. Good to high enantioselectivity was observed in an acetone–water solvent system, the system leading to (R)-alcohols of 80–96% ee. Enantioselectivity can be affected by the presence of the double bond in the unsaturated acetate prepared from an alkenol. The increased enantioselectivity observed for an acetone–water reaction system was utilized in the synthesis of optically active natural products possessing alkan-2-ol skeletons, such as (2R,6R,10R)-6,10,14-trimethylpentadecan-2-ol, the natural form of the sex pheromone of Corcyra cephalonica, and (R)-sulcatol, an aggregation pheromone of ambrosia beetles.