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, Kenichi 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
Publication statusPublished - 2003

Fingerprint

Nitriles
Cycloaddition
Oxides
Carbohydrates
Derivatives
benzonitrile

Keywords

  • [3+2] cycloadditions
  • Asymmetric synthesis
  • Chiral auxiliary
  • D-glucose
  • Nitrile oxides

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Highly Stereoselective [3+2] Cycloadditions of Nitrile Oxides to Methyl 4-O-Acryloyl-6-deoxy-2,3-O-(t-butyldimethylsilyl)-α-D-glucopyranoside. / Tamai, Tetsuo; Asano, Shingo; Totani, Kiichiro; Takao, Kenichi; Tadano, Kin Ichi.

In: Synlett, No. 12, 2003, p. 1865-1867.

Research output: Contribution to journalArticle

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