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 language | English |
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Pages (from-to) | 1363-1374 |
Number of pages | 12 |
Journal | Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry |
Volume | 69 |
Issue number | 12 |
DOIs | |
Publication status | Published - 2011 |
Externally published | Yes |
Keywords
- 1,4-conjugate additions
- All-carbon asymmetric quaternary carbon
- Chiral templates
- Diels-Alder reactions
- Sugar derivatives
ASJC Scopus subject areas
- Organic Chemistry