4.7 Article

Natural carbolines inspired the discovery of chiral CarOx ligands for asymmetric synthesis and antifungal leads

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 7, Issue 16, Pages 2263-2268

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo00519c

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Funding

  1. National Key R&D Program of China [2018YFD0201000]
  2. National Natural Science Foundation of China [21772094, 21977049]
  3. Natural Science Foundation of Jiangsu Province [BK20191306]

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The unprecedented beta-CarOxligands were conceived by the hybridization of alangiobussinine and the privileged pyridine-oxazoline scaffold. They performed well in the highly enantioselective Pd-catalyzed Michael addition of arylboronic acids to nitrostyrenes and beta-substituted cyclic enone (up to 99% ee). The beta-CarOxligands also showed an enhanced antifungal effect compared to alangiobussinine, demonstrating promising antifungal leads againstSclerotinia sclerotiorum.

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