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Biocatalytic Approaches for the Synthesis of Enantiopure Epoxides

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Biocatalysis - From Discovery to Application

Part of the book series: Topics in Current Chemistry ((4143,volume 200))

Abstract

Because of their high chemical versatility, enantiopure epoxides, as well as their corresponding vicinal diols, are recognized as being high value intermediates in fine organic chemistry, in particular for the synthesis of biologically active compounds in optically pure form.Therefore, research work aimed to set up efficient procedures allowing for the preparation of such target molecules has been intensively developed recently, leading to the emergence of various new methods based on either conventional chemistry or on biocatalytic reactions. In this review, we will focus on the use of such enzymatic approaches for the synthesis of enantiopure epoxides. Examination of the recent literature indicates that two general strategies have thus been developed, i.e. (a) the formation of the epoxide ring itself from an appropriate precursor (in general the corresponding olefin) and (b) the resolution of racemic substrates already bearing an oxirane ring. Several of these approaches have been shown to allow the synthesis of epoxides of different structures,which were thus obtained in enantiomerically enriched or even enantiopure form.

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Authors and Affiliations

  1. Groupe Biocatalyse et Chimie Fine, ERS 157 associée au CNRS, Faculté des Sciences de Luminy, Case 901, 163 Avenue de Luminy, F-13288, Marseille Cedex 9, France

    A. Archelas & R. Furstoss

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  1. A. Archelas
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  2. R. Furstoss
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  1. Institut für Organische Chemie, Technische Universität Darmstadt, Petersenstratße 22, D-64287, Darmstadt, Germany

    Wolf-Dieter Fessner

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Archelas, A., Furstoss, R. (1999). Biocatalytic Approaches for the Synthesis of Enantiopure Epoxides. In: Fessner, WD., et al. Biocatalysis - From Discovery to Application. Topics in Current Chemistry, vol 200. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-68116-7_6

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  • DOI: https://doi.org/10.1007/3-540-68116-7_6

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