Syntheses of medium-sized cyclic ethers from carbohydrates via an intramolecular nitrile oxide-alkene cycloaddition strategy

Tony K.M. Shing, Yong Li Zhong

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Theregioselectivity of intramolecular 1,3-dipolar cycloadditions of nitrile oxides prepared from 3-O-alkenyl-1,2-O-isopropylidene-α-D- pentodialdofuranoses is dependent on the length of the alkenyl chain. 3-O-Homoallyl nitrile oxide afforded exo-cyclization oxepane exclusively. 3-O-Pentenyl nitrile oxide produced a mixture of exo- and endo-cyclization adducts (oxocane and oxonane) whereas 3-O-hexenyl, heptenyl, and octenyl oxides all gave endo-cyclization adducts (ten-, eleven-, and twelve-membered cyclic ethers, respectively) exclusively.

Original languageEnglish
Pages (from-to)1205-1208
Number of pages4
JournalSynlett
Issue number8
DOIs
Publication statusPublished - 2006 May 15

Keywords

  • Carbohydrates
  • Cycloadditions
  • Ethers
  • Nitrile oxides
  • Stereoselective synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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