Formation and utility of azasilacyclopentadienes derived from silacyclopropenes and nitriles

Org Lett. 2009 Jan 15;11(2):425-8. doi: 10.1021/ol802412b.

Abstract

The copper-catalyzed insertions of nitriles into the Si-C bonds of silacyclopropenes provide azasilacyclopentadienes, which can be converted to allylic amines after reduction and protodesilylation. The enamine functionality of azasilacyclopentadienes also participates in 1,4-addition reactions and undergoes a hydroboration and oxidation sequence to form an allylic 1,2-amino alcohol.

Publication types

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

MeSH terms

  • Amines / chemistry
  • Amino Alcohols / chemistry
  • Aza Compounds / chemistry*
  • Boric Acids / chemistry
  • Carbon / chemistry
  • Catalysis
  • Copper / chemistry
  • Cyclopentanes / chemistry*
  • Nitriles / chemistry*
  • Silicon / chemistry*

Substances

  • Amines
  • Amino Alcohols
  • Aza Compounds
  • Boric Acids
  • Cyclopentanes
  • Nitriles
  • Carbon
  • Copper
  • boric acid
  • Silicon