Highly enantioselective organocatalytic Michael addition of nitroalkanes to 4-oxo-enoates

Chem Commun (Camb). 2009 Jul 28:(28):4251-3. doi: 10.1039/b905033g. Epub 2009 Jun 10.

Abstract

A useful Michael addition reaction using nitroalkanes as the nucleophile and 4-oxo-enoates as the Michael acceptor has been disclosed, and the reaction allows expedient access to functionalized chiral gamma-keto esters in high yields and excellent enantioselectivities (up to 98% ee), with a low catalyst loading.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanes / chemistry*
  • Butyrates / chemistry*
  • Catalysis
  • Crystallography, X-Ray
  • Models, Molecular
  • Nitro Compounds / chemistry*
  • Organic Chemicals / chemistry*
  • Stereoisomerism

Substances

  • 6-(nitrooxy)hexyl-(2z)-4-(acetyloxy)-3-(4-(methylsulfonyl)phenyl)-2-phenylbut-2-enoate
  • Alkanes
  • Butyrates
  • Nitro Compounds
  • Organic Chemicals