Some stereoselective carbon-carbon bond-forming reactions realized by using sugar-derived chiral templates

Kiichiro Totani, Ken Ichi Takao, Kin Ichi Tadano

Research output: Contribution to journalReview article

1 Citation (Scopus)

Abstract

In this article, the authors summarize a variety of stereoselective carbon-carbon bond-forming reactions realized by the use of sugar-derived chiral templates, which have been one of the active concerns in the authors' group in these fifteen years. Representative chiral templates prepared from D-glucose, D-galactose, or D-mannose are introduced first. Then, the utility of these templates for stereoselective carbon-carbon bond-forming reactions are outlined. These reactions include, 1) 1,4-conjugate additions, 2) α-alkylations of esters, 3) Diels-Alder cycloadditions, 4) 1,3-dipolar cycloadditions, and 5) α,α-dialkylation for the construction of an all-carbon asymmetric quaternary center. The use of a D-glucose derivative equipped with two bulky silyl ethers at C2 and C3 is emphasized throughout the article as the most effective chiral template.

Original languageEnglish
Pages (from-to)1363-1374
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume69
Issue number12
DOIs
Publication statusPublished - 2011 Dec 1
Externally publishedYes

Keywords

  • 1,4-conjugate additions
  • All-carbon asymmetric quaternary carbon
  • Chiral templates
  • Diels-Alder reactions
  • Sugar derivatives

ASJC Scopus subject areas

  • Organic Chemistry

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