A Simple Method for Asymmetric Trifluoromethylation of N-Acyl Oxazolidinones via Ru-Catalyzed Radical Addition to Zirconium Enolates

被引：113

作者：

Herrmann, Aaron T. ^{[1
]}

Smith, Lindsay L. ^{[1
]}

Zakarian, Armen ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 16期

基金：

美国国家科学基金会;

关键词：

ENANTIOSELECTIVE ALPHA-TRIFLUOROMETHYLATION; CARBON BOND FORMATION; SOFT ENOLIZATION; DIASTEREOSELECTIVE TRIFLUOROMETHYLATION; PERFLUOROALKYLATION REACTIONS; MEDICINAL CHEMISTRY; TRIETHYLBORANE; FLUORINATION; ALDEHYDES; COMPLEX;

D O I：

10.1021/ja302552e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Ru-catalyzed direct thermal trifluoromethylation and perfluoroalkylation of N-acyloxazolidinones has been developed. The reaction is experimentally simple and requires inexpensive reagents while providing good yields of products with good levels of stereocontrol. Preliminary studies have shown notable compatibility with functional groups, aromatics, and certain heteroaromatic substituents. The described method provides a useful alternative for the synthesis of fluorinated materials in an experimentally convenient manner.

引用

页码：6976 / 6979

页数：4

共 42 条

[41] NEW METHOD FOR TRIFLUOROMETHYLATION OF ENOLATE ANIONS AND APPLICATIONS TO REGIOSELECTIVE, DIASTEREOSELECTIVE AND ENANTIOSELECTIVE TRIFLUOROMETHYLATION
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[42] Direct carbon-carbon bond formation via chemoselective soft enolization of thioesters: A remarkably simple and versatile crossed-Claisen reaction applied to the synthesis of LY294002
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Lim, Daniel
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