Enantioselective formal [2+2] cycloaddition of ketenes with nitroso compounds catalyzed by N-heterocyclic carbenes

Org Biomol Chem. 2010 Nov 7;8(21):5007-11. doi: 10.1039/c0ob00249f. Epub 2010 Sep 1.

Abstract

Chiral N-heterocyclic carbenes were found to be efficient catalysts for the formal [2+2] cycloaddition reaction of alkyl(aryl)ketenes and nitroso compounds to give the corresponding 1,2-oxazetidin-3-ones in moderate to good yields with high enantioselectivities. Reductive ring-opening of the oxazetidinones give the corresponding α-hydroxy acid derivatives in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Ketones / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Nitroso Compounds / chemistry*
  • Stereoisomerism

Substances

  • Ketones
  • Nitroso Compounds
  • carbene
  • Methane