An entry to vinylcyclopropane through palladium-catalyzed intramolecular cyclopropanation of alkenes with unstabilized allylic tosylhydrazones

Chem Commun (Camb). 2015 Apr 11;51(28):6179-82. doi: 10.1039/c5cc00235d.

Abstract

A diastereoselective Pd-catalyzed intramolecular cyclopropanation of alkenes with unstabilized allylic tosylhydrazones was developed. This methodology provides an efficient entry toward synthesis of the bicyclo[3.1.0] hexane system with an exo-double bond, and sets the basis for future elaboration of more complex polycyclic motifs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Bridged Bicyclo Compounds / chemical synthesis
  • Bridged Bicyclo Compounds / chemistry
  • Catalysis
  • Cyclopentanes / chemical synthesis*
  • Cyclopentanes / chemistry*
  • Hydrazones / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry
  • Stereoisomerism
  • Tosyl Compounds / chemistry*

Substances

  • Alkenes
  • Bridged Bicyclo Compounds
  • Cyclopentanes
  • Hydrazones
  • Organometallic Compounds
  • Tosyl Compounds
  • bicyclo(3.1.0)hexane
  • Palladium