Enantioselective Rh-catalyzed domino transformations of alkynylcyclohexadienones with organoboron reagents

Org Lett. 2013 Mar 1;15(5):1148-51. doi: 10.1021/ol400363f. Epub 2013 Feb 20.

Abstract

A new enantioselective rhodium-catalyzed domino reaction is described that gives access to fused heterocycles by desymmetrization of alkyne-tethered cyclohexadienones. Two new C-C bonds and two stereocenters are formed in one step with good enantioselectivity. In contrast to prior reports, it was found that a vinylidene is not involved in the product formation but that syn-addition of the rhodium-aryl species onto the alkyne takes place.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Boron Compounds / chemistry*
  • Catalysis
  • Cyclohexanes / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Indicators and Reagents
  • Molecular Structure
  • Rhodium / chemistry
  • Stereoisomerism

Substances

  • Alkynes
  • Boron Compounds
  • Cyclohexanes
  • Heterocyclic Compounds
  • Indicators and Reagents
  • Rhodium