Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine

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 (compo...

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Published in:Organic & biomolecular chemistry 2011-12, Vol.9 (23), p.8171-8177
Main Authors: Muñoz, Lourdes, Rodriguez, Anna M, Rosell, Gloria, Bosch, M Pilar, Guerrero, Angel
Format: Article
Language:English
Subjects:
Amphetamine - chemistry
Kinetics
Molecular Structure
Phenethylamines - chemical synthesis
Phenethylamines - metabolism
Stereoisomerism
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description 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.
doi_str_mv 10.1039/c1ob06251d
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subjects Amphetamine - chemistry
Kinetics
Molecular Structure
Phenethylamines - chemical synthesis
Phenethylamines - metabolism
Stereoisomerism
title Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine
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