Rhodium-catalyzed 1,3-acyloxy migration and subsequent intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne

Chem Commun (Camb). 2012 Feb 21;48(16):2204-6. doi: 10.1039/c2cc17406e. Epub 2012 Jan 17.

Abstract

A Rh-catalyzed 1,3-acyloxy migration of propargyl ester followed by intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne was developed. This tandem reaction provides access to bicyclic compounds containing a highly functionalized isotoluene or cyclohexenone structural motif, while only aromatic compounds were observed in related transition metal-catalyzed cycloadditions.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkadienes / chemistry*
  • Alkynes / chemistry*
  • Bridged Bicyclo Compounds / chemistry
  • Catalysis
  • Cyclization
  • Rhodium / chemistry*

Substances

  • Alkadienes
  • Alkynes
  • Bridged Bicyclo Compounds
  • propadiene
  • Rhodium