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Enantioselective decarboxylative chlorination of β-ketocarboxylic acids
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Enantioselective decarboxylative chlorination of β-ketocarboxylic acids
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Journal Article
Enantioselective decarboxylative chlorination of β-ketocarboxylic acids
2017
Overview
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 S
N
2 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.
Due to the synthetic utility of the products, stereoselective halogenation is a powerful method for the synthesis of chiral compounds. Here the authors report an enantioselective decarboxylative chlorination, giving access to a range of α-chloroketones.
Publisher
Nature Publishing Group UK,Nature Publishing Group,Nature Portfolio
