Allylation reactions of aldehydes with allylboronates in aqueous media: unique reactivity and selectivity that are only observed in the presence of water

S Kobayashi, T Endo, T Yoshino…

Index: Kobayashi, Shu; Endo, Toshimitsu; Yoshino, Takumi; Schneider, Uwe; Ueno, Masaharu Chemistry - An Asian Journal, 2013 , vol. 8, # 9 p. 2033 - 2045

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Citation Number: 4

Abstract

Abstract 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 and kinetic studies were performed. The key intermediate, an allylzinc species, ...