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

Kazumasa Kitahara; Haruna Mizutani; Seiji Iwasa; Kazutaka Shibatomi

doi:10.1055/s-0039-1690009

Synthesis, Table of Contents

Synthesis 2019; 51(23): 4385-4392
DOI: 10.1055/s-0039-1690009

special topic

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

Kazumasa Kitahara

,

Haruna Mizutani

,

Seiji Iwasa

,

Kazutaka Shibatomi ∗

Department of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan Email: shiba@chem.tut.ac.jp

› Author Affiliations

Abstract

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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.

Key words

decarboxylative chlorination - chiral amine catalyst - enantioselective synthesis - β-ketocarboxylic acids - fluorinated compounds

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References

References

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