Highly stereoselective Diels-Alder reactions achieved on some hexopyranosidic templates

T. Nagatsuka, S. Yamaguchi, K. Totani, Kenichi 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
Publication statusPublished - 2001

Fingerprint

Carbohydrates
Cyclopentanes
Acrylics
Esters
Derivatives
5-norbornene-2-methanol
2-norbornene

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Nagatsuka, T., Yamaguchi, S., Totani, K., Takao, K., & Tadano, K. I. (2001). Highly stereoselective Diels-Alder reactions achieved on some hexopyranosidic templates. Synlett, (4), 481-484.

Highly stereoselective Diels-Alder reactions achieved on some hexopyranosidic templates. / Nagatsuka, T.; Yamaguchi, S.; Totani, K.; Takao, Kenichi; Tadano, K. I.

In: Synlett, No. 4, 2001, p. 481-484.

Research output: Contribution to journalArticle

Nagatsuka, T, Yamaguchi, S, Totani, K, Takao, K & Tadano, KI 2001, 'Highly stereoselective Diels-Alder reactions achieved on some hexopyranosidic templates', Synlett, no. 4, pp. 481-484.
Nagatsuka, T. ; Yamaguchi, S. ; Totani, K. ; Takao, Kenichi ; Tadano, K. I. / Highly stereoselective Diels-Alder reactions achieved on some hexopyranosidic templates. In: Synlett. 2001 ; No. 4. pp. 481-484.
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