Allylation of aldehydes and imines: promoted by reuseable polymer-supported sulfonamide of N-glycine

Org Lett. 2006 Feb 16;8(4):633-6. doi: 10.1021/ol0528235.

Abstract

[reaction: see text] A allylation of aldehydes and imines (generated in situ from aldehydes and amines) with allyltributyltin promoted by recoverable and reusable the polymer-supported sulfonamide of N-glycine has been developed. Good to high yields were obtained in various cases. Most of the SnBu(3) residue can be recovered as Bu(3)SnCl. Highly stereoselective synthesis of N-Boc-(2S,3S)-3-hydroxy-2-phenylpiperidine 7 was achieved by using the P4a-mediated allylation of Boc-l-phenylglycinal as a key step.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Glycine / analogs & derivatives*
  • Glycine / chemistry*
  • Imines / chemistry*
  • Molecular Structure
  • Organotin Compounds / chemistry
  • Piperidines / chemical synthesis*
  • Polymers / chemistry
  • Stereoisomerism
  • Sulfonamides / chemistry*

Substances

  • Aldehydes
  • Imines
  • N-Boc-(2S,3S)-3-hydroxy-2-phenylpiperidine
  • Organotin Compounds
  • Piperidines
  • Polymers
  • Sulfonamides
  • Glycine