Stereoselective synthesis of tetrasubstituted (Z)-alkenes from aryl alkyl ketones utilizing the Horner-Wadsworth-Emmons reaction

Chem Pharm Bull (Tokyo). 2002 Sep;50(9):1300-2. doi: 10.1248/cpb.50.1300.

Abstract

Tetrasubstituted (Z)-alkenes were readily prepared through the Horner-Wadsworth-Emmons reactions of methyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate with aryl alkyl ketones by employing Sn(OSO(2)CF(3))(2) and N-ethylpiperidine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 8-Hydroxy-2-(di-n-propylamino)tetralin / analogs & derivatives*
  • 8-Hydroxy-2-(di-n-propylamino)tetralin / chemistry
  • Alkenes / chemical synthesis*
  • Catalysis
  • Cinnamates / chemistry*
  • Cinnamates / isolation & purification
  • Indicators and Reagents
  • Ketones / chemical synthesis*
  • Methylation
  • Piperidines
  • Stereoisomerism

Substances

  • Alkenes
  • Cinnamates
  • Indicators and Reagents
  • Ketones
  • Piperidines
  • butyl-3,5-dimethoxy-4-hydroxycinnamate
  • isopropyl 3,5-dimethoxy-4-hydroxycinnamate
  • 8-(((trifluoromethyl)sulfonyl)oxy)-2-(n-propylamino)tetralin
  • 8-Hydroxy-2-(di-n-propylamino)tetralin
  • 1-ethylpiperidine