Stereoselective synthesis of dioxabicycles from 1-C-allyl-2-O-benzyl- glycosides - An intramolecular cyclization between 2-O-benzyl oxygen and the allyl double bond

An Tai Wu, Tian Yi, Huawu Shao, Shih Hsiung Wu, Wei Zou

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Addition of a proton to the double bond of 1-C-allyl-O-benzylglycosides gave a 2′-carbonium ion, which in turn reacted intramolecularly, in a regio- and diastereo-selective manner, with the nucleophilic oxygen of the 2-O-benzyl group to form an oxonium intermediate. Subsequent cleavage of the benzyl C-O bond led to dioxabicycles in moderate yields. Surprisingly, opposite diastereoselectivities were observed from 1-C-allylglycojfuranosides and 1-C-allylglycopyranosides, which produced 2,2′-trans- and 2,2′-cis-dioxabicycles, respectively.

Original languageEnglish
Pages (from-to)597-602
Number of pages6
JournalCanadian Journal of Chemistry
Volume84
Issue number4
DOIs
Publication statusPublished - 2006 Apr 1

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this