Application of the intramolecular isomerisation-aldolisation from allylic alcohols and allylic silyl ethers to the synthesis of indanones and indenones

Chemistry. 2007;13(26):7374-84. doi: 10.1002/chem.200700613.

Abstract

A new access to indanones was discovered through a one-step nickel or iron-mediated transposition of 2-hydroxyisobenzofurans. Starting from the corresponding silylenol ethers, a new one-pot tandem isomerisation-Mukaiyama aldol process was also developed. These versatile strategies will be useful for the preparation of various types of indanones and indenones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Allyl Compounds / chemistry*
  • Benzofurans / chemistry
  • Catalysis
  • Crystallography, X-Ray
  • Hydrolysis
  • Indans / chemistry*
  • Iron / chemistry
  • Isomerism
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Nickel / chemistry
  • Stereoisomerism

Substances

  • Alcohols
  • Allyl Compounds
  • Benzofurans
  • Indans
  • Nickel
  • Iron