Highly efficient, facile, room temperature intermolecular [5 + 2] cycloadditions catalyzed by cationic rhodium(I): one step to cycloheptenes and their libraries

Org Lett. 2010 Apr 2;12(7):1604-7. doi: 10.1021/ol100337m.

Abstract

A cationic rhodium(I) complex--[(C(10)H(8))Rh(cod)](+) SbF(6)(-)--catalyzes the remarkably efficient intermolecular [5 + 2] cycloaddition of vinylcyclopropanes (VCPs) and various alkynes, providing cycloheptene cycloadducts in excellent yields in minutes at room temperature. The efficacy and selectivity of this catalyst are also shown in a novel diversification strategy, affording a cycloadduct library in one step from nine commercially available components.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Cations / chemistry
  • Cyclization
  • Cycloheptanes / chemical synthesis*
  • Cycloheptanes / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Rhodium / chemistry*
  • Small Molecule Libraries
  • Stereoisomerism
  • Temperature*

Substances

  • Cations
  • Cycloheptanes
  • Organometallic Compounds
  • Small Molecule Libraries
  • Rhodium