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
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
收藏
页码:6976 / 6979
页数:4
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