Issue 23, 2011
From the journal:

Organic & Biomolecular Chemistry

Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine†

Lourdes Muñoz,‡a   Anna M. Rodriguez,‡a   Gloria Rosell,b   M. Pilar Boscha  and  Angel Guerrero*a  

* Corresponding authors

a Department of Biological Chemistry and Molecular Modelling, IQAC (CSIC), 08034 Barcelona, Spain
E-mail: angel.guerrero@iqac.csic.es
Fax: (+34)-932045904
Tel: (+34)-934006120

b Unit of Medicinal Chemistry (Associated to CSIC), Faculty of Pharmacy, University of Barcelona, Av. Diagonal s/n, 08028 Barcelona, Spain

Abstract

Both enantiomers of several phenylethylamines, structurally related to amphetamine, have been prepared in good yields and excellent enantiomeric purity by enzymatic kinetic resolution using CAL-B and ethyl methoxyacetate as the acyl donor. In the case of the 4-hydroxyderivative of amphetamine (compound 4i), the S enantiomer racemized possibly in a dynamic kinetic resolution (DKR) under the enzymatic conditions used.

Graphical abstract: Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine

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Article information

DOI
https://doi.org/10.1039/C1OB06251D
Article type
Paper
Submitted
25 Jul 2011
Accepted
30 Aug 2011
First published
31 Aug 2011

Org. Biomol. Chem., 2011,9, 8171-8177

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Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine

L. Muñoz, A. M. Rodriguez, G. Rosell, M. P. Bosch and A. Guerrero, Org. Biomol. Chem., 2011, 9, 8171 DOI: 10.1039/C1OB06251D

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