Diastereoselective alkynylation of N-p-tolylsulfinylimines with aluminum acetylides

J Org Chem. 2007 Oct 12;72(21):7893-7. doi: 10.1021/jo071139w. Epub 2007 Sep 19.

Abstract

The addition of alkynyl dimethyl aluminum compounds onto N-p-tolylsulfinylimines was investigated. The reaction was proved to be totally regioselective, leading to propargylamines with high diastereoselectivity (up to 99% de). Addition of aluminum derivatives gave a reversal of diastereoselectivity compared to the addition reaction of lithium acetylide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Aluminum / chemistry*
  • Imines / chemistry*
  • Lithium / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Pargyline / analogs & derivatives*
  • Pargyline / chemical synthesis
  • Pargyline / chemistry
  • Propylamines / chemical synthesis*
  • Propylamines / chemistry
  • Stereoisomerism
  • Sulfoxides / chemistry*

Substances

  • Alkynes
  • Imines
  • Organometallic Compounds
  • Propylamines
  • Sulfoxides
  • propargylamine
  • Lithium
  • Pargyline
  • Aluminum