Sodium phenoxide-phosphine oxides as extremely active lewis base catalysts for the mukaiyama aldol reaction with ketones

被引：62

作者：

Hatano, Manabu ^{[1
]}

Takagi, Ed ^{[1
]}

Ishihara, Kazuaki ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Nagoya, Aichi 4648603, Japan

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 22期

基金：

美国国家航空航天局;

关键词：

D O I：

10.1021/ol702052r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A highly efficient Mukaiyama aldol reaction between ketones and trimethylsilyl enolates catalyzed by sodium phenoxide-phosphine oxides as simple homogeneous Lewis base catalysts (0.5-10 mol %) was developed, which minimized competing retro-aldol reaction. For a variety of aromatic ketones and aldimines, aldol and Mannich-type products with an a-quaternary carbon center were obtained in good to excellent yields. Up to 100 mmol scale of benzophenone and trimethylsilyl enolate with 0.5 mol % of catalyst was established in 97% yield (34.8 g).

引用

页码：4527 / 4530

页数：4

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