Issue 70, 2015
From the journal:

RSC Advances

Exploiting sequential lipase-catalyzed reactions to achieve enantiomerically pure chiral primary alcohols†

Rodrigo S. Martins,a   Anees Ahmad,a   Luiz F. Silva, Jr.a  and  Leandro H. Andrade*a  

* Corresponding authors

a Universidade de São Paulo, Instituto de Química, Av. Prof. Lineu Prestes 748, São Paulo, Brazil
E-mail: leandroh@iq.usp.br

Abstract

The lipase-catalyzed enantioselective acetylation of benzofused cycloalkane-containing primary alcohols with vinyl acetate was performed and allowed the isolation of enantiopure alcohols. Lipases from P. cepacia, C. rugosa, C. antarctica, P. fluorescens, C. cylindracea and M. miehei exhibited remarkable activity towards acetylation of these alcohols, affording the corresponding acetates with high conversion. Due to the high lipase activity toward primary alcohols, the enantioselectivity was low. To circumvent this problem, sequential kinetic resolution was employed with enantiocomplementary lipases leading to enantiomerically pure primary alcohols. This method represents a new approach to obtain chiral building blocks bearing ring systems, such as indanes, chromanes and tetralins.

Graphical abstract: Exploiting sequential lipase-catalyzed reactions to achieve enantiomerically pure chiral primary alcohols

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Article information

DOI
https://doi.org/10.1039/C5RA06469D
Article type
Paper
Submitted
10 Apr 2015
Accepted
22 Jun 2015
First published
22 Jun 2015

RSC Adv., 2015,5, 56599-56605

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Exploiting sequential lipase-catalyzed reactions to achieve enantiomerically pure chiral primary alcohols

R. S. Martins, A. Ahmad, L. F. Silva and L. H. Andrade, RSC Adv., 2015, 5, 56599 DOI: 10.1039/C5RA06469D

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