Enantiocomplementary Preparation of (S)- and (R)-Arylalkylcarbinols by Lipase-Catalysed Resolution and Mitsunobu Inversion: Impact of Lipase Amount

Catalysts

Nassima Bouzemi¹  Ismahane Grib¹  Zahia Houiene¹ 

[1]Ecocompatible Asymmetric Catalysis Laboratory (LCAE), Department of Chemistry, Badji Mokhtar Annaba-University, B.P. 12, 23000 Annaba, Algeria

关键词: deracemisation;    lipase;    hydrolysis;    stereoinversion;    arylalkylcarbinol;   

DOI  :  10.3390/catal4030215

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.