Pd-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols via capture of active tautomers

被引：42

作者：

Chen, Zhang-Pei ^{[1
]}

Chen, Mu-Wang ^{[1
]}

Shi, Lei ^{[1
]}

Yu, Chang-Bin ^{[1
]}

Zhou, Yong-Gui ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China

来源：

CHEMICAL SCIENCE | 2015年 / 6卷 / 06期

基金：

中国国家自然科学基金;

关键词：

HIGHLY ENANTIOSELECTIVE HYDROGENATION; HETEROAROMATIC-COMPOUNDS; PYRIDINIUM SALTS; PERFLUOROALKYLATION REACTIONS; ISOQUINOLINIUM SALTS; ANTIBACTERIAL AGENTS; KINETIC RESOLUTION; AZOMETHINE IMINES; BRONSTED ACIDS; QUINOLINES;

D O I：

10.1039/c5sc00835b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient palladium-catalyzed asymmetric hydrogenation of fluorinated aromatic pyrazol-5-ols has been developed via capture of the active tautomers. A wide variety of 2,5-disubstituted and 2,4,5-trisubstituted pyrazolidinones have been synthesized with up to 96% and 95% ee, respectively. The hydrogenation pathway includes Bronsted acid promoted tautomerization of pyrazol-5-ols and Pd-catalyzed asymmetric hydrogenation of the active tautomer.

引用

页码：3415 / 3419

页数：5

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