Enantioselective direct aldol reaction of α-keto esters catalyzed by (S(a))-binam-D-prolinamide under quasi solvent-free conditions

Org Biomol Chem. 2012 May 28;10(20):4029-35. doi: 10.1039/c2ob25224d. Epub 2012 Apr 18.

Abstract

(S(a))-Binam-D-prolinamide (20 mol%), instead of (S(a))-binam-L-prolinamide, in combination with chloroacetic acid (100 mol%) is an efficient organocatalyst for the direct aldol reaction between α-keto esters as electrophiles and alkyl and α-functionalised ketones, under quasi solvent-free conditions, providing access to highly functionalised chiral quaternary γ-keto α-hydroxyesters with up to 92% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Esters / chemistry*
  • Ketones / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Proline / analogs & derivatives*
  • Proline / chemistry*
  • Solvents / chemistry
  • Stereoisomerism

Substances

  • (S(a))-binam-D-prolinamide
  • Esters
  • Ketones
  • Solvents
  • Proline