Oxazoline-substituted prolinamide-based organocatalysts for the direct intermolecular aldol reaction between cyclohexanone and aromatic aldehydes

Academic Article

Abstract

  • Oxazoline-substituted prolinamides catalyse the direct asymmetric aldol reaction between cyclohexanone and a range of aldehydes to give excellent conversions and enantioselectivities up to 84% under optimum conditions. Reactions were highly substrate-specific with electron-deficient aldehydes giving the highest yields and ee values. The absolute configuration of the 4-chlorobenzaldehyde-derived product was unequivocally established as (2S,1′R) by single-crystal X-ray analysis, and the stereochemistry of the product was shown to be determined principally by the stereochemistry of the proline fragment. © Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
  • Authors

    Digital Object Identifier (doi)

    Author List

  • Doherty S; Knight JG; McRae A; Harrington RW; Clegg W
  • Start Page

  • 1759
  • End Page

  • 1766
  • Issue

  • 10