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α-Alkylation of ketones by addition of zinc enamides to unactivated olefins

M Nakamura, T Hatakeyama…

文献索引:Nakamura, Masaharu; Hatakeyama, Takuji; Nakamura, Eiichi Journal of the American Chemical Society, 2004 , vol. 126, # 38 p. 11820 - 11825

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被引用次数: 32

摘要

A zinc enamide generated from the corresponding N-aryl imine undergoes addition to an unactivated olefin, such as ethylene, 1-octene, and isobutylene, to generate an α-alkylated γ- zincioimine intermediate in good to excellent yield. Terminal and gem-disubstituted olefins react with> 99% regioselectivity, allowing the CC bond formation to take place at the more hindered carbon of the double bond. The organozinc intermediate undergoes further CC ...