Copper(I)-catalyzed aryl or vinyl addition to electron-deficient alkenes cascaded by cationic cyclization

Org Lett. 2014 Mar 7;16(5):1322-5. doi: 10.1021/ol500033w. Epub 2014 Feb 19.

Abstract

An exoselective copper-catalyzed arylation- and vinylation-carbocyclization of electron-deficient alkenes was developed to provide rapid and efficient access to a variety of functionalized 3,3-disubstituted oxindoles. With this method, a highly efficient and concise formal synthesis of (±)-physostigmine and (±)-physovenine has been completed.

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Cations
  • Copper / chemistry*
  • Cyclization
  • Electrons
  • Indoles / chemistry
  • Molecular Structure
  • Oxindoles
  • Physostigmine / analogs & derivatives*
  • Physostigmine / chemical synthesis*
  • Physostigmine / chemistry
  • Stereoisomerism

Substances

  • Alkenes
  • Cations
  • Indoles
  • Oxindoles
  • 2-oxindole
  • physovenine
  • Copper
  • Physostigmine
  • cuprous chloride