Functionalization of an sp(3) C-H bond via a redox-neutral domino reaction: diastereoselective synthesis of hexahydropyrrolo[2,1-b]oxazoles

Chem Commun (Camb). 2014 Mar 18;50(22):2951-3. doi: 10.1039/c4cc00454j. Epub 2014 Feb 6.

Abstract

A diastereoselective synthesis of pyrrolidinooxazolidines was achieved by a metal-free, base-promoted reaction of pyrrolidine and aromatic aldehydes under microwave irradiation. The rare functionalization of an sp(3) C-H bond probably results from an in situ generated azomethine ylide that undergoes cycloaddition with aldehydes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry
  • Hydrogen / chemistry
  • Microwaves
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry
  • Oxidation-Reduction
  • Potassium Acetate / chemistry
  • Stereoisomerism
  • Toluene / chemistry

Substances

  • Oxazoles
  • Toluene
  • Carbon
  • Hydrogen
  • Potassium Acetate