Synthesis of highly functionalized biaryls by condensation of 2-fluoro-1,3-bis(silyloxy) 1,3-dienes with 3-cyanochromones and subsequent domino "retro-Michael/aldol/fragmentation"

J Org Chem. 2010 Dec 3;75(23):8315-8. doi: 10.1021/jo1018443. Epub 2010 Nov 9.

Abstract

The Me(3)SiOTf-mediated condensation of 1-ethoxy-2-fluoro-1,3-bis(trimethylsilyloxy) 1,3-dienes with 3-cyanochromones afforded 3-cyano-2-(4-ethoxy-3-fluoro-2,4-dioxobutyl)chroman-4-ones. Their reaction with triethylamine afforded fluorinated azaxanthones or biaryls. The product distribution depends on the structure of the diene. The formation of the biaryls can be explained by an unprecedented domino "retro-Michael/aldol/fragmentation" reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromones / chemical synthesis*
  • Chromones / chemistry*
  • Crystallography, X-Ray
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Polyenes / chemical synthesis*
  • Polyenes / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Chromones
  • Polyenes