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

Takayuki Nagatsuka, Shuhei Yamaguchi, Kiichiro Totani, Ken Ichi Takao, Kin Ichi Tadano

Research output: Contribution to journalArticle

13 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 Nov 30

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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