2011 年 69 巻 12 号 p. 1363-1374
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.