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

M Nakamura, T Hatakeyama…

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

Full Text: HTML

Citation Number: 32

Abstract

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 ...