Click-Dimerized Cinchona Alkaloids

J Org Chem. 2016 Sep 2;81(17):8029-34. doi: 10.1021/acs.joc.6b01403. Epub 2016 Aug 12.

Abstract

A series of Cinchona alkaloid-derived dimers were obtained in high yields in copper-catalyzed 1,3-dipolar "click" cycloaddition using bis(TMS)butadiyne and other bivalent alkynes. The products with bitriazole linkers were effective ligands for asymmetric copper-catalyzed Michael addition. It was shown that the presence of such linker was responsible for effective chirality transfer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Cinchona Alkaloids / chemistry*
  • Click Chemistry*
  • Copper / chemistry
  • Cycloaddition Reaction
  • Dimerization
  • Proton Magnetic Resonance Spectroscopy
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Alkynes
  • Cinchona Alkaloids
  • Copper