Domino reactions consisting of heterocyclization and 1,2-migration-redox-neutral and oxidative transition-metal catalysis

Angew Chem Int Ed Engl. 2011 Oct 10;50(42):9965-8. doi: 10.1002/anie.201103961. Epub 2011 Sep 7.

Abstract

Two cats, two paths: two novel domino reactions starting from 6-hydroxy-2-alkyl-2-alkynylcyclohexanones have been discovered. While redox-neutral platinum catalysis gives rise to furans through a sequence of cyclization, 1,2-shift, and Grob fragmentation, oxidative copper catalysis provides an entry to bicyclic 2,3-dihydrofurans. Upon cyclization and oxidation, an unusual benzilic acid rearrangement can take place in this case.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction
  • Transition Elements / chemistry*

Substances

  • Furans
  • Organometallic Compounds
  • Transition Elements