Asymmetric Synthesis of α-Chloro-α-halo Ketones by Decarboxylative Chlorination of α-Halo-β-ketocarboxylic Acids

被引：14

作者：

Kitahara, Kazumasa ^{[1
]}

Mizutani, Haruna ^{[1
]}

Iwasa, Seiji ^{[1
]}

Shibatomi, Kazutaka ^{[1
]}

机构：

[1] Toyohashi Univ Technol, Dept Appl Chem & Life Sci, 1-1 Hibarigaoka,Tempaku Cho, Toyohashi, Aichi 4418580, Japan

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 23期

关键词：

decarboxylative chlorination; chiral amine catalyst; enantio-selective synthesis; beta-ketocarboxylic acids; fluorinated compounds; QUATERNARY STEREOGENIC CENTERS; ENANTIOSELECTIVE FLUORINATION; CONSTRUCTION; ESTERS; KETOESTERS; LIGANDS;

D O I：

10.1055/s-0039-1690009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral alpha-chloro-alpha-fluoro ketones were synthesized by enantio-selective decarboxylative chlorination of alpha-chloro-beta-ketocarboxylic acids in the presence of a chiral amine catalyst. The reaction yielded the corresponding alpha-chloro-alpha-fluoro ketones with moderate-to-high enantioselectivity (up to 90% ee). The method was also applied to the synthesis of alpha-bromo-alpha-chloro ketones with 90% ee.

引用

页码：4385 / 4392

页数：8

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