Enantiocomplementary preparation of (S)-and (R)-Arylalkylcarbinols by Lipase-Catalysed resolution and mitsunobu inversion: Impact of lipase amount

Abstract

A series of arylalkylcarbinol derivatives were deracemized through sequential combination of Candida antarctica lipase B (CAL-B) catalyzed resolution by hydrolysis and Mitsunobu stereoinversion. The (S)-acetates were obtained in 71%-99% ee and 76%-89% yields. An enantiocomplementarity was established for the hydrolysis and acylation reactions with CAL-B lipase. Thus, the (S) and (R) enantiomers of Indan-1-yl acetate, 1,2,3,4-tetrahydro-1-naphthalenol acetate and 1-(2-naphthyl) ethyl acetate were obtained in 91%-99% ee and 76%-89% yield. © 2014 by the authors; licensee MDPI, Basel, Switzerland.