Highly stereoselective synthesis of 1,2,3-trisubstituted indanes via oxidative N-heterocyclic carbene-catalyzed cascades

Org Lett. 2011 Sep 16;13(18):4966-9. doi: 10.1021/ol202108a. Epub 2011 Aug 24.

Abstract

Three stereocenters are formed in the carbene catalyzed cascade reaction of enals with various β-diketones to give the corresponding indane derivatives with excellent stereoselectivities. The products are readily transformed to the corresponding 1,2,3-trisubstituted indane derivatives, which represent privileged substructures in medicinal chemistry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Heterocyclic Compounds / chemistry*
  • Indans / chemical synthesis*
  • Indans / chemistry
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Heterocyclic Compounds
  • Indans
  • carbene
  • Methane