Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides

Takayuki Nagatsuka, Shuhei Yamaguchi, Kiichiro Totani, Kenichi Takao, Kin ichi Tadano

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The Diels-Alder reactions of a variety of hexopyranosides carrying an acrylic ester with cyclopentadiene were examined. Some acrylic esters provided the cycloaddition products carrying a norbornene carboxylate with a high level of diastereoselectivity. Plausible mechanisms are presented for the cases of a 4-O-acryloyl-6-deoxy-α-D-glucopyranosidic and 2-O-acryloyl-α-D-glucopyranosidic substrates. By reductive removal of the carbohydrate templates from the adducts, either 2S or 2R-enriched 5-norbornene-2-methanol were obtained.

Original languageEnglish
Pages (from-to)519-535
Number of pages17
JournalJournal of Carbohydrate Chemistry
Volume20
Issue number7-8
DOIs
Publication statusPublished - 2001

Fingerprint

Cycloaddition Reaction
Acrylics
Esters
Cyclopentanes
Cycloaddition
Carbohydrates
Substrates
2-norbornene
5-norbornene-2-methanol

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Organic Chemistry

Cite this

Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides. / Nagatsuka, Takayuki; Yamaguchi, Shuhei; Totani, Kiichiro; Takao, Kenichi; Tadano, Kin ichi.

In: Journal of Carbohydrate Chemistry, Vol. 20, No. 7-8, 2001, p. 519-535.

Research output: Contribution to journalArticle

Nagatsuka, Takayuki ; Yamaguchi, Shuhei ; Totani, Kiichiro ; Takao, Kenichi ; Tadano, Kin ichi. / Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides. In: Journal of Carbohydrate Chemistry. 2001 ; Vol. 20, No. 7-8. pp. 519-535.
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