Highly stereoselective Diels-Alder reactions achieved on some hexopyranosidic templates

T. Nagatsuka, S. Yamaguchi, K. Totani, K. I. Takao, K. I. Tadano

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The Diels-Alder reactions of some carbohydrate derivatives, as chiral acrylic esters, with cyclopentadiene proceed highly diastereoselectively to provide the adducts carrying a norbornene carboxylate. By reductive removal of the carbohydrate templates from the adducts, both 2S and 2R-enriched 5-norbornene-2-methanol are obtained.

Original languageEnglish
Pages (from-to)481-484
Number of pages4
JournalSynlett
Issue number4
DOIs
Publication statusPublished - 2001

Keywords

  • Asymmetric synthesis
  • Cyclopentadiene
  • Diastereoselectivity
  • Diels-Alder reaction
  • Norbornene derivatives

ASJC Scopus subject areas

  • Organic Chemistry

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