Allenylphosphonates/allenylphosphine oxides as intermediates/precursors for intramolecular cyclization leading to phosphorus-based indenes, indenones, benzofurans, and isochromenes

J Org Chem. 2012 Jun 15;77(12):5345-56. doi: 10.1021/jo300705f. Epub 2012 Jun 6.

Abstract

Utilizing internally available functional groups, a simple protocol for the efficient synthesis of phosphorus-based indenes, indenones, benzofurans, and isochromenes via intramolecular cyclization of allene intermediates/precursors is generated; the latter intermediates/precursors are conveniently obtained through aldehyde-, alkylidene-, and hydroxyl-functionalized propargyl alcohols and P(III)-Cl precursors. The structures of key products have been unequivocally confirmed by X-ray crystallography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzofurans / chemical synthesis*
  • Benzofurans / chemistry*
  • Benzopyrans / chemical synthesis*
  • Benzopyrans / chemistry*
  • Catalysis
  • Cyclization
  • Indenes / chemical synthesis*
  • Indenes / chemistry*
  • Molecular Structure
  • Organophosphorus Compounds / chemical synthesis*
  • Organophosphorus Compounds / chemistry*
  • Phosphines / chemistry*
  • Stereoisomerism

Substances

  • Benzofurans
  • Benzopyrans
  • Indenes
  • Organophosphorus Compounds
  • Phosphines