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

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Glycosides
Cyclization
Protons
Ions
Oxygen
hydronium ion

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

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title = "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",
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.",
author = "Wu, {An Tai} and Tian Yi and Huawu Shao and Wu, {Shih Hsiung} and Wei Zou",
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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. / Wu, An Tai; Yi, Tian; Shao, Huawu; Wu, Shih Hsiung; Zou, Wei.

In: Canadian Journal of Chemistry, Vol. 84, No. 4, 01.04.2006, p. 597-602.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 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

AU - Wu, An Tai

AU - Yi, Tian

AU - Shao, Huawu

AU - Wu, Shih Hsiung

AU - Zou, Wei

PY - 2006/4/1

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AB - 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.

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