Highly Stereoselective [3+2] Cycloadditions of Nitrile Oxides to Methyl 4-O-Acryloyl-6-deoxy-2,3-O-(t-butyldimethylsilyl)-α-D-glucopyranoside

Tetsuo Tamai, Shingo Asano, Kiichiro Totani, Ken Ichi Takao, Kin Ichi Tadano

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

The [3+2] cycloadditions of benzonitrile oxide or pivalonitrile oxide to methyl 4-O-acryloyl-6-deoxy-2,3-di-O-(t-butyldimethylsilyl)-α -D-glucopyranoside provided the respective adducts, each as virtually a single diastereomer. By reductive removal of the carbohydrate template from each adduct, the respective (R)-enriched Δ2-isoxazoline derivative was obtained.

Original languageEnglish
Pages (from-to)1865-1867
Number of pages3
JournalSynlett
Issue number12
DOIs
Publication statusPublished - 2003 Jan 1

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Keywords

  • Asymmetric synthesis
  • Chiral auxiliary
  • D-glucose
  • Nitrile oxides

ASJC Scopus subject areas

  • Organic Chemistry

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