Synthesis and cyclodehydration of hydroxyphenols: a new stereoselective approach to 3-aryl-2,3-dihydrobenzofurans

J Org Chem. 2007 Sep 28;72(20):7761-4. doi: 10.1021/jo070316q. Epub 2007 Sep 7.

Abstract

A novel and simple method for the stereoselective synthesis of substituted 3-aryl-2,3-dihydrobenzofurans by intramolecular cyclization of hydroxyphenols is described. The stereoselective ortho-C-alkylation of phenols allows a novel and stereoselective access to a diverse array of polyfunctionalized products containing a diarylmethane stereogenic center without the need for time-consuming protection-deprotection steps.

MeSH terms

  • Benzofurans / chemical synthesis*
  • Cyclization
  • Epoxy Compounds / chemistry
  • Phenols / chemistry*
  • Stereoisomerism

Substances

  • Benzofurans
  • Epoxy Compounds
  • Phenols