Enantioselective α-Hydroxylation by Modified Salen-Zirconium(IV)-Catalyzed Oxidation of β-Keto Esters

被引：30

作者：

Yang, Fan ^{[1
]}

Zhao, Jingnan ^{[1
]}

Tang, Xiaofei ^{[1
]}

Zhou, Guangli ^{[1
]}

Song, Wangze ^{[1
]}

Meng, Qingwei ^{[1
]}

机构：

[1] Dalian Univ Technol, Sch Pharmaceut Sci & Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 03期

基金：

中国国家自然科学基金;

关键词：

CINCHONA ALKALOID DERIVATIVES; QUATERNARY AMMONIUM-SALTS; DICARBONYL COMPOUNDS; ASYMMETRIC CATALYSIS; MOLECULAR-OXYGEN; OXO ESTERS; KETOESTERS; OXINDOLES;

D O I：

10.1021/acs.orglett.6b03554

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly enantioselective alpha-hydroxylation of beta-keto esters using cumene hydroperoxide (CHP) as the oxidant was realized by a chiral (1S,2S)-cyclohexanediamine backbone salen-zirconium(IV) complex as the catalyst. A variety of corresponding chiral alpha-hydroxy beta-keto esters were obtained in excellent yields (up to 99%) and enantio-selectivities (up to 98% ee). The zirconium-catalyzed enantioselective alpha-hydroxylation of beta-keto esters was scalable, and the zirconium catalyst was recyclable. The reaction can be performed in gram scale, and corresponding chiral products were acquired in 95% yield and 99% ee.

引用

页码：448 / 451

页数：4

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