三乙基镓作为一种非亲核碱，用于从酮类生成烯醇盐。
Triethylgallium as a nonnucleophilic base to generate enolates from ketones.
作者信息
Nishimura Yoshio, Miyake Yutaka, Amemiya Ryo, Yamaguchi Masahiko
机构信息
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai 980-8578, Japan.
出版信息
Org Lett. 2006 Oct 26;8(22):5077-80. doi: 10.1021/ol061948m.
PMID:17048847
Abstract
Triethylgallium deprotonated cyclic and acyclic ketones at 125-175 degrees C without forming carbonyl addition products, and the resulting gallium enolates underwent facile C-benzoylation and an aldol reaction. Unsymmetrical ketones were preferentially enolized at the methylene moiety, which was under kinetic control. [reaction: see text]
摘要
三乙基镓在125 - 175摄氏度下使环状和非环状酮去质子化，且未形成羰基加成产物，生成的镓烯醇盐易于发生C - 苯甲酰化反应和羟醛缩合反应。不对称酮优先在亚甲基部分烯醇化，这是受动力学控制的。[反应：见原文]
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