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

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 establishe...

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Bibliographic Details
Published in:Catalysts
Main Authors: Nassima Bouzemi, Ismahane Grib, Zahia Houiene, Louisa Aribi-Zouioueche
Format: Article in Journal/Newspaper
Language:English
Published: MDPI AG 2014
Subjects:
deracemisation
lipase
hydrolysis
stereoinversion
arylalkylcarbinol
Chemical technology
TP1-1185
Chemistry
QD1-999
Antarc*
Antarctica
Online Access:https://doi.org/10.3390/catal4030215
https://doaj.org/article/961bbdb87ace4b85b3875bcf60cb0d92
Description
Summary: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.

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