Stereoselective synthesis of cis-2,5-disubstituted pyrrolidines via Wacker-type aerobic oxidative cyclization of alkenes with tert-butanesulfinamide nucleophiles

Org Lett. 2012 Mar 2;14(5):1242-5. doi: 10.1021/ol3000519. Epub 2012 Feb 21.

Abstract

Palladium(II)-catalyzed aerobic oxidative cyclization of alkenes with tethered tert-butanesulfinamides furnishes enantiopure 2,5-disubstituted pyrrolidines, originating from readily available and easily diversified starting materials. These reactions are the first reported examples of metal-catalyzed addition of sulfinamide nucleophiles to alkenes.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemistry*
  • Butanes / chemistry*
  • Catalysis
  • Cyclization
  • Molecular Structure
  • Oxidation-Reduction
  • Pyrrolidines / chemical synthesis*
  • Stereoisomerism
  • Sulfonamides / chemistry*

Substances

  • Alkenes
  • Butanes
  • Pyrrolidines
  • Sulfonamides
  • tert-butanesulfinamide