(+)-1(S), 5(R), 8(S)-8-phenyl-2-azabicyclo[3.3.0]octan-8-ol n,o-methylboronate (2) and its enantiomer, chiral chemzymes which serve as catalysts for their own enantioselective synthesis

https://doi.org/10.1016/S0040-4039(01)93796-7Get rights and content

Abstract

An efficient synthesis of (+)-1(S), 5(R), 8(S)-8-phenyl-2-azabicyclo[3.3.0]octan-8-ol (1) and its enantiomer is described. The B-methyloxazaborolidine derivatives (2) of these amino alcohols are excellent catalysts (chemzymes) for the enantioselective reduction of a variety of achiral ketones to chiral secondary alcohols, e.g. acetophenone, 98% ee; pinacolone, 98% ee; α-tetralone, 97% ee; and 2-bromo-2-cyclohexen-1-one, 98% ee. The oxazaborolidine 2 is a catalyst for the enantioselective synthesis of 14, a starting material for the synthesis of chiral 2 itself.

References (9)

  • E.J. Corey and G.A. Reichard, Tetrahedron Letters,...
  • J.A. Dale et al.

    J. Am. Chem. Soc.

    (1973)
  • E.J. Corey et al.

    J. Am. Chem. Soc.

    (1987)
    E.J. Corey et al.

    J. Am. Chem. Soc.

    (1987)
    E.J. Corey et al.

    J. Org. Chem.

    (1988)
    E.J. Corey
There are more references available in the full text version of this article.

Cited by (0)

View full text