Proline-based reduced dipeptides as recyclable and highly enantioselective organocatalysts for asymmetric Michael addition

Org Biomol Chem. 2011 Oct 7;9(19):6487-90. doi: 10.1039/c1ob05679d. Epub 2011 Aug 9.

Abstract

A series of novel proline-based reduced dipeptides was developed and evaluated for a direct Michael addition of ketones and aldehydes to nitroalkenes. Excellent yields (up to 95%), diastereoselectivities (up to 98% dr) and enantioselectivities (up to 98% ee) were achieved in the presence of 5 mol% catalyst without any additional additives at room temperature.

MeSH terms

  • Aldehydes / chemistry
  • Alkenes / chemistry
  • Catalysis
  • Dipeptides / chemical synthesis*
  • Dipeptides / chemistry
  • Ketones / chemistry
  • Molecular Structure
  • Nitro Compounds / chemistry
  • Proline / chemistry*
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Alkenes
  • Dipeptides
  • Ketones
  • Nitro Compounds
  • Pyrans
  • Proline