HIGHLY ENANTIOSELECTIVE SYNTHESIS OF LONG-CHAIN ALKYL TRIFLUOROMETHYLCARBINOLS AND BETA-THIOTRIFLUOROMETHYL CARBINOLS THROUGH LIPASES

Among a variety of lipases tested, Candida antarctica lipase has been found to promote the enantioselective acylation of long chain alkyl tr ifluoromethyl carbinols 1a-4a and beta-thiotrifluoromethyl carbinols 5 a-7a, producing both R and S enantiomeric alcohols in good to excellen t chemical yield and enantioselectivity. In all cases the lipase prefe rentially acylates the S enantiomer, irrespective the presence or not of a sulfur atom in beta position to the hydroxyl group, When the reac tion was carried out on the non-fluorinated substrates 1c-2c, the proc ess occurred much faster and with higher e.e. of the less reacting ena ntiomer than when conducted on the fluorinated substrates. Copyright ( C) 1996 Elsevier Science Ltd