A regio- and diastereoselective palladium-catalyzed cyclopropanation of norbornene derivatives with molecular oxygen as the sole oxidant

Chem Commun (Camb). 2012 Oct 25;48(83):10340-2. doi: 10.1039/c2cc35124b.

Abstract

A mild and efficient Pd-catalyzed cyclopropanation of norbornene derivatives with tertiary propargylic alcohols using molecular oxygen as the sole oxidant is described. This process allows quick and atom-economical assembly of various 1,2,3-trisubstituted cyclopropanes bearing α,β-unsaturated ketone moieties in high yields as a single regio- and diastereoisomer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclopropanes / chemistry*
  • Molecular Structure
  • Norbornanes / chemical synthesis*
  • Norbornanes / chemistry
  • Organometallic Compounds / chemistry*
  • Oxidants / chemistry*
  • Oxygen / chemistry*
  • Palladium / chemistry*
  • Stereoisomerism

Substances

  • Cyclopropanes
  • Norbornanes
  • Organometallic Compounds
  • Oxidants
  • Palladium
  • Oxygen