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

✍ Scribed by Inés Petschen; Edi A. Malo; M.P. Bosch; Angel Guerrero

• Book ID: 103977565
• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 501 KB
• Volume: 7
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/0957-4166(96)00256-x

✦ Synopsis

Among a variety of lipases tested, C ~i d a antarctica lipase has been found to promote the enantioselective acylation of long chain alkyl trifluoromethyl carbinols la-4a and 13thiotrifluoromethyl 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 [3 position to the hydroxyl group. When the reaction was carried out on the non-fluorinated substrates lc-2e, the process occurred much faster and with higher e.e. of the less reacting enantiomer than when conducted on the fluorinated substrates.