Development of Grignard-Type Addition Reaction and Application of Its into the Practical Synthetic Process

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This summary presents the research results of development of Grignard-type addition reaction and application of its into the practical synthetic process.1) Allyation of aldehydes by using allylic halides in the presence of metallic bismuth.2) A Grignard-type addition of allyl unit to carbonyl compounds containing a carboxyl group by using bismuth trichloride-metallic zinc-allyl bromide.3) Allylation of aldehydes by using allylic halides prepared in situ from allylic alcohols in the presence of metallic bismuth.4) A novel aqueous Barbier-Grignard-type allylation of aldehydes in a metallic magnesium/bismuth trichloride bimetal system.5) Allylation of carbonyl compounds by using allyl Grignard reagent and various metallic salts in aqueous media.6) Allylation of aldehydes by using allyltin compounds and allylbismuth compounds in aqueous media or water.7) Asymmetric allylation of carbonyl compounds by using tetraallyltin.8) Bismuth mediated allylation of unprotected carbohydrates.9) Solvent-mediated chemoselective reduction of aldehydes by using tributyltin hydride in methanol, aqueous organic solvents, or water: an environmentally benign process.10) Solvent-free one-pot reduction of imines generated in situ from aldehydes and aniline by tributyltin hydride on silica gel.