Mo(CO)6-mediated intramolecular Pauson-Khand reaction of substituted diethyl 3-allyloxy-1-propynylphosphonates

J Org Chem. 2009 Feb 6;74(3):1029-33. doi: 10.1021/jo801988k.

Abstract

Cyclisation of diethyl 3-allyloxy-1-propynylphosphonates with Mo(CO)(6) under PK conditions to give 3-substituted-5-oxo-3,5,6,6a-tetrahydro-1H-cyclopenta[c]furan-4-ylphosphonate, 2a-h, in 45-88% isolated yields was done. The R groups are always syn with H(b) (where applicable). The stereochemistry was determined via both NMR and crystal X-ray analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemical synthesis
  • Alkynes / chemistry*
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Carbon Monoxide / chemistry
  • Crystallography, X-Ray
  • Cyclization
  • Ligands
  • Molecular Structure
  • Molybdenum / chemistry*
  • Organophosphonates / chemical synthesis
  • Organophosphonates / chemistry*

Substances

  • Alkynes
  • Bridged Bicyclo Compounds, Heterocyclic
  • Ligands
  • Organophosphonates
  • methylacetylene
  • Carbon Monoxide
  • Molybdenum