RCM-mediated synthesis of trifluoromethyl-containing nitrogen heterocycles

J Org Chem. 2006 Sep 29;71(20):7527-32. doi: 10.1021/jo060893z.

Abstract

A ring-closing metathesis mediated pathway to trifluoromethyl-containing piperidines is detailed. This involves the development of a synthetic route to a new (trifluoromethyl)allylating reagent via a Diels-Alder/retro-Diels-Alder strategy, its application in the synthesis of a series of trifluormethyl-substituted diolefin precursors for ring-closing metathesis, and eventually the successful cyclization of these precursor molecules into the corresponding functionalized piperidines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chlorofluorocarbons, Methane
  • Cyclization
  • Heterocyclic Compounds / chemical synthesis*
  • Nitrogen
  • Piperidines / chemical synthesis*

Substances

  • Chlorofluorocarbons, Methane
  • Heterocyclic Compounds
  • Piperidines
  • Nitrogen
  • fluoroform