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Issue 24, 2009
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Towards a chemo-enzymatic method for the asymmetric synthesis of β-amino tertiary alcohols

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Abstract

The synthesis of a number of β-amino tertiary alcohols has been achieved via ring-opening of an unsymmetrical epoxide with primary and secondary amines. The results revealed that primary amines give symmetrical triol products following an undesired acyl migration reaction, whereas secondary amines give the desired chiral (racemic) products. Furthermore, we demonstrate that asymmetric products can be formed using enantiomerically pure epoxide and aromatic amines without any loss of enantiomeric excess.

Graphical abstract: Towards a chemo-enzymatic method for the asymmetric synthesis of β-amino tertiary alcohols

  • This article is part of the themed collection: Biocatalysis
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Publication details

The article was received on 05 Aug 2009, accepted on 16 Sep 2009 and first published on 15 Oct 2009


Article type: Paper
DOI: 10.1039/B916013B
Citation: Org. Biomol. Chem., 2009,7, 5163-5165
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    Towards a chemo-enzymatic method for the asymmetric synthesis of β-amino tertiary alcohols

    A. March-Cortijos and T. J. Snape, Org. Biomol. Chem., 2009, 7, 5163
    DOI: 10.1039/B916013B

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