Diastereoselective synthesis of 4,5'-bis-proline compounds via reductive dimerization of N-acyloxyiminium ions

J Org Chem. 2007 Mar 2;72(5):1814-7. doi: 10.1021/jo062406l. Epub 2007 Jan 31.

Abstract

A short, practical synthesis of novel, unsymmetrical 4,5'-bis-proline compounds has been achieved, highlighted by the application of an unprecedented samarium diiodide-driven regio- and diastereocontrolled reductive dimerization of N-acyloxyiminium ions generated from readily available 2-methoxy-5-silyloxymethyl-N-Boc pyrrolidines. The title proline dimers proved to be pertinent metal-free catalysts in aldol and Mannich reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Imines / chemistry*
  • Mannich Bases / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Oxidation-Reduction
  • Proline / analogs & derivatives*
  • Proline / chemical synthesis*
  • Proline / chemistry
  • Samarium / chemistry
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared
  • Stereoisomerism

Substances

  • Imines
  • Mannich Bases
  • Samarium
  • Proline