4.8 Article

Unnatural Amino Acid Synthesis Enabled by the Regioselective Cobalt(III)-Catalyzed Intermolecular Carboamination of Alkenes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 48, Pages 15166-15170

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201608729

Keywords

alkene difunctionalization; carboamination; Cp*Co(III) catalysis; redox-neutral conditions; unnatural amino acids

Funding

  1. Deutsche Forschungsgemeinschaft

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Herein, we report an unprecedented regioselective and entirely atom-economic cobalt(III)-catalyzed method for the non-annulative, intermolecular carboamination of alkenes. The methodology enables the direct synthesis of unnatural amino acid derivatives and proceeds under redox-neutral conditions with a completely regioselective C-C bond and C-N bond formation. Furthermore, this reaction exemplifies the inherently different mechanistic behavior of the Cp*Co-III catalyst and its Cp*Rh-III counterpart, especially towards beta-H-elimination.

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