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Asymmetric Synthesis of α-Chloro-α-halo Ketones by Decarboxylative Chlorination of α-Halo-β-ketocarboxylic Acids
Synthesis ( IF 2.2 ) Pub Date : 2019-07-23 , DOI: 10.1055/s-0039-1690009
Kazumasa Kitahara , Haruna Mizutani , Seiji Iwasa , Kazutaka Shibatomi 1
Affiliation  

Published as part of the Special Topic Halogenation methods (with a view towards radioimaging applications)

Abstract

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

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



中文翻译:

α-卤代-β-酮羧酸的脱羧氯化反应不对称合成α-氯代-α-卤代酮

作为特殊主题卤化方法的一部分发布(以放射成像应用为目的)

抽象的

在手性胺催化剂的存在下,通过α-氯-β-酮羧酸的对映选择性脱羧氯化反应,合成了手性α-氯-α-氟代酮。反应产生具有中等至高对映选择性(至多90%ee)的相应α-氯-α-氟代酮。该方法还用于ee为90%的α-溴-α-氯代酮的合成。

在手性胺催化剂的存在下,通过α-氯-β-酮羧酸的对映选择性脱羧氯化反应,合成了手性α-氯-α-氟代酮。反应产生具有中等至高对映选择性(至多90%ee)的相应α-氯-α-氟代酮。该方法还用于ee为90%的α-溴-α-氯代酮的合成。

更新日期:2019-07-23
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