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Auto-tandem catalysis: facile synthesis of substituted alkylidenecyclohexanones by domino (4+2) cycloaddition-elimination reaction

Chem Commun (Camb). 2010 Nov 21;46(43):8246-8. doi: 10.1039/c0cc03336g. Epub 2010 Sep 28.

Abstract

A catalytic domino reaction producing substituted 2-alkylidenecyclohexanone from 3-oxymethyl-2-siloxy-1,3-butadienes, which can be prepared from Baylis-Hillman adducts, and α,β-unsaturated ketones is described. The process involves two mechanistically distinct reactions, (4+2) cycloaddition and elimination. Both of these reactions are catalyzed by Tf(2)NH.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Butadienes / chemistry
  • Catalysis
  • Cyclohexanones / chemical synthesis
  • Cyclohexanones / chemistry*
  • Ketones / chemistry
  • Mesylates / chemistry

Substances

  • Butadienes
  • Cyclohexanones
  • Ketones
  • Mesylates
  • triflic imide
  • 1,3-butadiene