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Zn(OH)2-catalyzed allylation reactions of aldehydes with allylboronates in aqueous media have been developed. In contrast to conventional allylboration reactions of aldehydes in organic solvents, the α-addition products were obtained exclusively. A catalytic cycle in which the allylzinc species was generated through a B-to-Zn exchange process is proposed… (More)
Zn(OH)(2)-catalyzed allylation reactions of allylboronates with aldehydes proceeded smoothly in aqueous media; when alpha-substituted allylboronates were employed, the alpha-addition products were obtained exclusively, and syn-adducts were formed selectively in most cases; the use of Zn(OH)(2) with dmp (ligand) in aqueous media is the key to these reactions.
Asymmetric catalysis is now recognized as one of the most efficient methods for the preparation of optically active compounds. Although many catalytic asymmetric reactions have been developed, most reactions are carried out under strictly anhydrous and oxygen-free conditions, because most chiral catalysts and reagents decompose in the presence of even small… (More)