Palladium-Catalyzed Synthesis of Substituted Prolines

  • ChemPubSoc Europe Logo
  • Author: Veronika Belusa
  • Published Date: 04 January 2015
  • Source / Publisher: European Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Palladium-Catalyzed Synthesis of Substituted Prolines

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Proline is arguably the most important amino acid. However, the direct functionalization of proline is surprisingly little explored. Zhanxiang Liu and Yuhong Zhang, Zhejiang University, Hangzhou, China, and colleagues have developed a highly effective synthesis of C-3-substituted prolines. They used Pd-catalyzed C(sp3)–H activation for the straightforward functionalization of prolines.

 

 

The use of an 8-aminoquinolinecarboxamide directing group allows direct arylation, alkenylation, and alkylation at the C-3 position of prolines in moderate to high yields with diverse iodo- or bromo precursors. This method should open up new avenues of research in biological chemistry and organocatalysis involving proline.


 

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