Cu(I)-catalyzed atom transfer radical cyclization of trichloroacetamides tethered to electron-deficient, -neutral, and -rich alkenes: synthesis of polyfunctionalized 2-azabicyclo[3.3.1]nonanes

Chem Commun (Camb). 2012 Sep 11;48(70):8799-801. doi: 10.1039/c2cc34133f. Epub 2012 Jul 26.

Abstract

A novel synthetic entry to 2-azabicyclo[3.3.1]nonanes based on a copper(I)-catalyzed intramolecular coupling of amino-tethered trichloroacetamides and unsaturated nitriles, esters and alkenes, as well as enol acetates, is described. A study of the reaction conditions and the scope of the process is reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetamides / chemistry
  • Alkanes / chemical synthesis*
  • Alkenes / chemistry
  • Azabicyclo Compounds / chemical synthesis*
  • Catalysis
  • Chloroacetates / chemistry
  • Copper / chemistry*
  • Cyclization
  • Cyclohexenes / chemistry*
  • Electrons
  • Esters
  • Magnetic Resonance Spectroscopy
  • Nitriles
  • Stereoisomerism

Substances

  • Acetamides
  • Alkanes
  • Alkenes
  • Azabicyclo Compounds
  • Chloroacetates
  • Cyclohexenes
  • Esters
  • Nitriles
  • Copper