Ytterbium(III) triflate-catalyzed amination of 1-cyclopropylprop-2-yn-1-ols as an expedient route to conjugated enynes

J Org Chem. 2009 Feb 20;74(4):1740-3. doi: 10.1021/jo8024626.

Abstract

Ytterbium(III) triflate-catalyzed ring opening of substituted 1-cyclopropyl-2-propyn-1-ols with sulfonamides as an efficient synthetic route to conjugated enynes is described herein. The reaction was operationally straightforward and accomplished in moderate to good yields and regioselective manner in all except one case under mild conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Amination
  • Catalysis
  • Cyclopropanes / chemistry*
  • Mesylates / chemistry*
  • Organometallic Compounds / chemistry*
  • Sulfonamides / chemistry

Substances

  • Alkynes
  • Cyclopropanes
  • Mesylates
  • Organometallic Compounds
  • Sulfonamides
  • ytterbium(III) triflate
  • cyclopropane