Issue 65, 2014
From the journal:

RSC Advances

Preparation of chiral glycerol derivatives using chemoenzymatic approaches†

Carmen Solarte,a   Mercè Balcells,a   Mercè Torres,b   Núria Salab  and  Ramon Canela-Garayoa ORCID logo *a  

* Corresponding authors

a Department of Chemistry, University of Lleida-Agrotecnio Center, Rovira Roure 191, Lleida, Spain
E-mail: canela@quimica.udl.cat
Fax: +34 973238264
Tel: +34 973 702843

b Department of Food Science and Technology, University of Lleida, Rovira Roure 191, Lleida, Spain

Abstract

Following our preparation of dissymmetric chlorohydrin esters from glycerol, we have used several lipases and whole cells to examine the kinetic resolution (KR) and dynamic kinetic resolution (DKR) of 3-chloro-2-hydroxypropyl esters. Regarding the KR, PS-IM, MmL and CALB lipases and whole cells of Aspergillus flavus showed the best selectivity and activity, depending on the compound studied. PS-IM allowed the isolation of (R)-3-chloro-2-hydroxypropyl pivaloate in 34% yield and with >99% enantiomeric excess (ee). DKR was carried out combining the biocatalysts that performed best for KR and suitable reaction conditions for racemization. Whole cells of A. flavus allowed the preparation of enantioenriched (S)-3-chloro-2-acetoxypropyl-2-methyl-2-phenyl propanoate in 43% yield and with 79% ee. Lipozyme from Mucor miehei used in a reaction subsequent to DKR allowed the purification of the corresponding enantioenriched (S)-3-chloro-2-acetoxypropyl pivaloate.

Graphical abstract: Preparation of chiral glycerol derivatives using chemoenzymatic approaches

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Article information

DOI
https://doi.org/10.1039/C4RA04515G
Article type
Paper
Submitted
13 May 2014
Accepted
31 Jul 2014
First published
01 Aug 2014

RSC Adv., 2014,4, 34623-34631

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Preparation of chiral glycerol derivatives using chemoenzymatic approaches

C. Solarte, M. Balcells, M. Torres, N. Sala and R. Canela-Garayoa, RSC Adv., 2014, 4, 34623 DOI: 10.1039/C4RA04515G

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