Enantioselective decarboxylative chlorination of β-ketocarboxylic acids

Kazutaka Shibatomi (), Kazumasa Kitahara, Nozomi Sasaki, Yohei Kawasaki, Ikuhide Fujisawa and Seiji Iwasa
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Kazutaka Shibatomi: Toyohashi University of Technology
Kazumasa Kitahara: Toyohashi University of Technology
Nozomi Sasaki: Toyohashi University of Technology
Yohei Kawasaki: Toyohashi University of Technology
Ikuhide Fujisawa: Toyohashi University of Technology
Seiji Iwasa: Toyohashi University of Technology

Nature Communications, 2017, vol. 8, issue 1, 1-7

Abstract: Abstract Stereoselective halogenation is a highly useful organic transformation for multistep syntheses because the resulting chiral organohalides can serve as precursors for various medicinally relevant derivatives. Even though decarboxylative halogenation of aliphatic carboxylic acids is a useful and fundamental synthetic method for the preparation of a variety of organohalides, an enantioselective version of this reaction has not been reported. Here we report a highly enantioselective decarboxylative chlorination of β-ketocarboxylic acids to obtain α-chloroketones under mild organocatalytic conditions. The present method is also applicable for the enantioselective synthesis of tertiary α-chloroketones. The conversions of the resulting α-chloroketones into α-aminoketones and α-thio-substituted ketones via SN2 reactions at the tertiary carbon centres are also demonstrated. These results constitute an efficient approach for the synthesis of chiral organohalides and are expected to enhance the availability of enantiomerically enriched chiral compounds with heteroatom-substituted chiral stereogenic centres.

Date: 2017
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DOI: 10.1038/ncomms15600

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