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
收藏
页码:4385 / 4392
页数:8
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