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Synthesis of pyrrolidine-3-carboxylic acid derivatives via asymmetric Michael addition reactions of carboxylate-substituted enones

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Abstract

To concisely synthesize highly enantiomerically enriched 5-alkyl-substituted pyrrolidine-3-carboxylic acids, organocatalytic enantioselective Michael addition reactions of 4-alkyl-substituted 4-oxo-2-enoates with nitroalkanes have been developed. Using the developed reaction method, 5-methylpyrrolidine-3-carboxylic acid with 97% ee was obtained in two steps.

Graphical abstract: Synthesis of pyrrolidine-3-carboxylic acid derivatives via asymmetric Michael addition reactions of carboxylate-substituted enones

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Publication details

The article was received on 20 Jun 2017, accepted on 30 Jun 2017 and first published on 30 Jun 2017


Article type: Communication
DOI: 10.1039/C7OB01484H
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Synthesis of pyrrolidine-3-carboxylic acid derivatives via asymmetric Michael addition reactions of carboxylate-substituted enones

    F. Yin, A. Garifullina and F. Tanaka, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01484H

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