Enantioselective transesterification of a tertiary alcohol by lipase A from Candida antarctica

✍ Scribed by Sajja Hari Krishna; Mattias Persson; Uwe T Bornscheuer

• Book ID: 104359544
• Publisher: Elsevier Science
• Year: 2002
• Tongue: English
• Weight: 88 KB
• Volume: 13
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(02)00739-5

✦ Synopsis

Chiral tertiary alcohols and their esters represent important flavor compounds and are useful building blocks. Unfortunately, they are accepted by only a few lipases/esterases as substrates and enantioselectivity is usually very low. We report here a highly enantioselective transesterification of the tertiary alcohol 2-phenylbut-3-yn-2-ol using lipase A from Candida antarctica (CAL-A). Under optimized conditions, the corresponding acetate was obtained with 94% ee at 35% conversion equivalent to an enantioselectivity factor of E=65. In contrast, satisfactory enantioselective hydrolysis of the racemic acetate was not feasible as this is very prone to autohydrolysis.