Cinchona Alkaloid-Catalyzed Asymmetric Trifluoromethylation of Alkynyl Ketones with Trimethylsilyl Trifluoromethane

被引：76

作者：

Kawai, Hiroyuki ^{[1
]}

Tachi, Kentaro ^{[1
]}

Tokunaga, Etsuko ^{[1
]}

Shiro, Motoo ^{[2
]}

Shibata, Norio ^{[1
]}

机构：

[1] Nagoya Inst Technol, Grad Sch Engn, Dept Frontier Mat, Showa Ku, Nagoya, Aichi 4668555, Japan

[2] Rigaku Corp, Tokyo 1968666, Japan

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 22期

关键词：

ENANTIOSELECTIVE TRIFLUOROMETHYLATION; TERTIARY ALCOHOLS; INHIBITORS; AROMATASE; CARBON; ALDEHYDES; SALT;

D O I：

10.1021/ol102189c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic enantioselective trifluoromethylation of alkynyl ketones 1 with (trifluoromethyl)trimethylsilane is disclosed by an operationally simple procedure, based on the combination of ammonium bromide of bis-cinchona alkaloids with Me4NF to afford trifluoromethyl-substituted tertiary propargyl alcohols (up to 96% ee), which are the important chiral building blocks for pharmaceuticals. Biologically attractive aryl heteroaryl trifluoromethyl carbinols were also synthesized.

引用

页码：5104 / 5107

页数：4

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