4.8 Article

Enantioselective Synthesis of Indole-Based Biaryl Atropisomers via Palladium-Catalyzed Dynamic Kinetic Intramolecular C-H Cyclization

Journal

ACS CATALYSIS
Volume 7, Issue 8, Pages 5316-5320

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b01855

Keywords

atropisomer; homogeneous catalysis; palladium; C-H cyclization; indole

Funding

  1. 973 project from the MOST of China [2015CB856600]
  2. NSFC [21472179, 21622206]
  3. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]

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We report here a palladium-catalyzed enantioselective synthesis of indole-based atropisomers via an intramolecular dynamic kinetic C-H cyclization. The TADDOL-derived phosphoramidite ligand proves to be most efficient in this directing-group-free transformation, delivering products with up to 96:4 er. The thermal stability of the axial chirality of the atropisomers has also been investigated.

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