Amine-catalyzed addition of azide ion to alpha,beta-unsaturated carbonyl compounds

Org Lett. 1999 Oct 7;1(7):1107-9. doi: 10.1021/ol9909076.

Abstract

[formula: see text] A new protocol for the beta-azidation of alpha,beta-unsaturated carbonyl compounds is described. The method employs tertiary amines as catalysts for azide addition. The azide source is a 1:1 mixture of TMSN3 and AcOH. Tertiary amines, either in solution or bound to a solid support, are efficient catalysts for the reaction.

Publication types

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

MeSH terms

  • Amines / chemistry*
  • Azides / chemistry*
  • Catalysis
  • Ions
  • Ketones / chemical synthesis*
  • Ketones / chemistry

Substances

  • Amines
  • Azides
  • Ions
  • Ketones