Straightforward and highly diastereoselective synthesis of 2,2-di-substituted perhydrofuro[2,3-b]pyran (and furan) derivatives promoted by BiCl3

Chem Commun (Camb). 2013 Aug 14;49(63):7085-7. doi: 10.1039/c3cc42292e.

Abstract

An effective and facile method for the synthesis of 2,2-di-substituted perhydrofuro[2,3-b]pyran (and furan) derivatives is described. The cyclization of 1,2-cyclopropanated sugars with olefins in the presence of BiCl3 is highly diastereoselective. 2,2-Di-substituted cyclization products were obtained in good to excellent yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Bismuth / chemistry*
  • Carbohydrates / chemistry
  • Chlorides / chemistry*
  • Crystallography, X-Ray
  • Cyclization
  • Furans / chemical synthesis
  • Furans / chemistry*
  • Molecular Conformation
  • Pyrans / chemical synthesis
  • Pyrans / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Carbohydrates
  • Chlorides
  • Furans
  • Pyrans
  • bismuth trichloride
  • Bismuth
  • furan