Organoplatinum complex promoted the asymmetric endo stereochemically controlled Diels-Alder reaction between 3-diphenylphosphinofuran and diphenylvinylphosphine

Inorg Chem. 2009 Dec 7;48(23):11394-8. doi: 10.1021/ic9014543.

Abstract

The organoplatinum complex containing ortho-metalated (R)-(1-(dimethylamino)ethyl)-naphthalene as the chiral auxiliary has been used efficiently to promote the asymmetric [4 + 2] Diels-Alder reaction between diphenylvinylphosphine and 3-diphenylphosphinofuran to generate two chelating diphosphine endocycloadducts in the ratio 17:1. The absolute configurations of the three newly generated stereocenters have been assigned by single-crystal X-ray analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chelating Agents / chemical synthesis
  • Chelating Agents / chemistry
  • Crystallography, X-Ray
  • Cyclization
  • Furans / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Organoplatinum Compounds / chemistry*
  • Phosphines / chemical synthesis
  • Phosphines / chemistry*
  • Stereoisomerism
  • Vinyl Compounds / chemistry*

Substances

  • 3-diphenylphosphinofuran
  • Chelating Agents
  • Furans
  • Organoplatinum Compounds
  • Phosphines
  • Vinyl Compounds
  • diphenylvinylphosphine