Highly enantioselective synthesis of long chain alkyl trifluoromethyl carbinols and β-thiotrifluoromethyl carbinols through lipases

Article abstract of DOI:10.1016/0957-4166(96)00256-X

Among a variety of lipases tested, Candida antarctica lipase has been found to promote the enantioselective acylation of long chain alkyl trifluoromethyl carbinols 1a-4a and β-thiotrifluoromethyl carbinols 5a-7a, producing both R and S enantiomeric alcohols in good to excellent chemical yield and enantioselectivity. In all cases the lipase preferentially acylates the S enantiomer, irrespective the presence or not of a sulfur atom in β position to the hydroxyl group. When the reaction was carried out on the non-fluorinated substrates 1c-2c, the process occurred much faster and with higher e.e. of the less reacting enantiomer than when conducted on the fluorinated substrates.