Highly efficient synthesis of functionalized tertiary alcohols catalyzed by potassium alkoxide-crown ether complexes

被引：20

作者：

Hatano, Manabu ^{[1
]}

Suzuki, Shinji ^{[1
]}

Takagi, Eri ^{[1
]}

Ishihara, Kazuaki ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4646603, Japan

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 26期

关键词：

ENANTIOSELECTIVE ALDOL ADDITIONS; PHOSPHINE OXIDES; TRIMETHYLSILYL ENOLATE; DIALKYL PHOSPHITES; CARBONYL-COMPOUNDS; RECENT PROGRESS; REAGENTS; KETONES; TRIFLUOROMETHYL; ALDEHYDES;

D O I：

10.1016/j.tetlet.2009.01.028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient Mukaiyama aldol reaction between ketones and trimethylsilyl enolates ill the presence of potassium alkoxide-crown ether complexes as Lewis base catalysts (0.3-5 mol%), which minimized the competing retro-aldol reaction, was developed. These catalysts promoted other addition reactions of trimethylsilyl reagents to ketones and aldimines, Such as silyltrifluoromethylation, silylcyanation, and silylphosphonylation. A direct hydrophosphonylation of ketones also proceeded when the catalysts were used as a Bronsted base under mild reaction conditions. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3171 / 3174

页数：4

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