Organocatalytic enantioselective desymmetrization of cyclic enones via phosphine promoted [3+2] annulations

Chem Commun (Camb). 2011 Jan 21;47(3):1015-7. doi: 10.1039/c0cc03164j. Epub 2010 Nov 9.

Abstract

Phosphine catalyzed enantioselective [3+2] cyclizations on 4-substituted 2,6-diarylidenecyclohexanones and 2,4-diarylidene-bicyclo[3.1.0]hexan-3-ones take place with high diastereo- and enantioselectivity levels. The process affords spirocyclic compounds with excellent stereochemical control of up to five stereogenic centres.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Cyclohexanones / chemical synthesis
  • Cyclohexanones / chemistry*
  • Hexanones / chemical synthesis
  • Hexanones / chemistry*
  • Models, Molecular
  • Phosphines / chemistry*
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry*
  • Stereoisomerism

Substances

  • Cyclohexanones
  • Hexanones
  • Phosphines
  • Spiro Compounds
  • phosphine