Elsevier

Tetrahedron Letters

Volume 37, Issue 1, 1 January 1996, Pages 39-42
Tetrahedron Letters

Enantioselective reduction of ketones by borane catalysed by oxazaphospholidine oxides

https://doi.org/10.1016/0040-4039(95)02078-0Get rights and content

Abstract

New enantioselective catalysts for the asymmetric reduction of ketones by borane are described. Easily prepared by oxidation of chiral oxazaphospholidines, these compounds increase sensitively the reduction rate of numerous ketones and induce ee's up to 94% in the case of the 2-chloroacetophenone.

Chiral oxazaphospholidine oxides efficiently catalyse the enantioselective reduction of ketones by borane with ee up to 94%:

  1. Download : Download full-size image

References (18)

  • G.J. Quallich et al.

    Tetrahedron Lett.

    (1993)
  • B. Burns et al.

    Tetrahedron Lett.

    (1993)
  • B. Burns et al.

    Tetrahedron: Asymmetry

    (1994)
  • T. Koizumi et al.

    Tetrahedron Lett.

    (1981)
  • A. Hirao et al.

    J. Chem. Soc., Chem. Commun.

    (1981)
  • S. Itsuno et al.

    J. Chem. Soc., Chem. Commun.

    (1983)
  • S. Itsuno et al.

    J. Chem. Soc., Perkin Trans. 1

    (1984)
  • E.J. Corey et al.

    J. Am. Chem. Soc.

    (1987)
  • E.J. Corey et al.

    J. Am. Chem. Soc.

    (1987)
There are more references available in the full text version of this article.

Cited by (38)

  • Asymmetric catalysis as a method for the synthesis of chiral organophosphorus compounds

    2014, Tetrahedron Asymmetry
    Citation Excerpt :

    The biosynthesis of phosphorus compounds was carried out using various yeasts, microscopic fungi, and bacteria that are sources of biocatalysts which can be isolated and used separately. The reduction of ketones with Saccharomyces cerevisiae, that is, Baker’s yeast, is the most studied and widely used method of bioconversion, because this biocatalyst is accessible and universal, and the process is easily realizable.76–90 Yeast-catalyzed asymmetric reduction of diethyl 2-oxoalkylphosphonates 124 and 126, respectively, led to 2-hydroxyalkylphosphonates 125 and 127, 128 obtained in good yields and with enantiopurity as high as about 97–100%.76,84

View all citing articles on Scopus
View full text