Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts

被引：22

作者：

Majdecki, Maciej ^{[1
]}

Grodek, Piotr ^{[1
]}

Jurczak, Janusz ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 01期

关键词：

ENANTIOSELECTIVE FLUORINATION; ASYMMETRIC FLUORINATION; KETOESTERS; TRIFLUOROMETHYLATION; CHEMISTRY; ADDITIONS; SALTS;

D O I：

10.1021/acs.joc.0c02486

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an enantioselective phase transfer alpha-chlorination of beta-keto esters catalyzed by hybrid amide-based Cinchona derivatives. The chlorination process proceeds with proper quantitative yields (up to <99%) and high asymmetric induction (up to 97% ee). We show that the use of only 0.5 mol % hybrid catalyst based on a Cinchona core allows the chlorination reaction to be conducted in a highly enantioselective manner with various indanone and tetralone carboxylate esters.

引用

页码：995 / 1001

页数：7

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