Regio- and stereoselectivity of the addition of O-, S-, N-, and C-nucleophiles to the beta vinyl oxirane derived from D-glucal

J Org Chem. 2004 Dec 10;69(25):8702-8. doi: 10.1021/jo048981b.

Abstract

6-O-Trityl- (1a) and 6-(O-benzyl)-substituted epoxide (1b) derived from D-glucal were examined in their addition reactions with O-, C-, N-, and S-nucleophiles. A 1,4-regio- and beta-stereoselective or an anti 1,2-addition pathway is commonly observed depending on the ability of the nucleophile to coordinate with the oxirane oxygen. When TMSN(3) or LiN(3) are used as azide-based nucleophiles, a 1,2-syn-addition pathway is also observed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Deoxyglucose / analogs & derivatives*
  • Deoxyglucose / chemistry*
  • Epoxy Compounds / chemical synthesis*
  • Ethylene Oxide / analogs & derivatives
  • Ethylene Oxide / chemical synthesis*
  • Molecular Conformation
  • Stereoisomerism
  • Vinyl Compounds / chemical synthesis*
  • Vinyl Compounds / chemistry*

Substances

  • Epoxy Compounds
  • Vinyl Compounds
  • d-glucal
  • Deoxyglucose
  • Ethylene Oxide