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Stereocontrolled Reduction of β-Ketoesters with Geotrichum Candidum

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Microbial Reagents in Organic Synthesis

Part of the book series: NATO ASI Series ((ASIC,volume 381))

Abstract

A local strain of Geotrichum candidum has been used to reduce simple β-ketoesters, variously α-substituted β-ketoesters and α-substituted nitroketones. In several examples, the stereochemistry of the asymmetric center(s) created in the resulting hydroxyester was completely controlled by using either fresh or “aged” mycelium, indicating the simultaneous operation of several reducing enzymes. Applications of this method are illustrated in the preparation, on a multigram scale, of optically pure asymmetric synthons (containing one or two asymmetric centers). In addition, a complete deracemization of simple β-hydroxyesters was demonstrated, indicating multiple oxidoreduction equilibria. The mechanism of such deracemization reactions is discussed.

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Authors and Affiliations

  1. Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques Unité associée au CNRS N°400, Université R.Descartes, 45 rue des Saints-Pères, 75270, Paris Cedex 06, France

    R. Azerad & D. Buisson

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  1. R. Azerad
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  2. D. Buisson
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  1. Dipartimento di Chimica, Politecnico di Milano, Milano, Italy

    Stefano Servi

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Azerad, R., Buisson, D. (1992). Stereocontrolled Reduction of β-Ketoesters with Geotrichum Candidum . In: Servi, S. (eds) Microbial Reagents in Organic Synthesis. NATO ASI Series, vol 381. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-2444-7_34

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  • DOI: https://doi.org/10.1007/978-94-011-2444-7_34

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