4.8 Article

Palladium(0)-Catalyzed Intermolecular Asymmetric Allylic Dearomatization of Polycyclic Indoles

Journal

ORGANIC LETTERS
Volume 20, Issue 3, Pages 748-751

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03887

Keywords

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Funding

  1. National Key Research and Development Program of China [2016YFA0202900]
  2. National Basic Research Program of China (973 Program) [2015CB856600]
  3. NSFC [21332009, 21421091, 21572252]
  4. Science and Technology Commission of Shanghai Municipality [16XD1404300]
  5. Chinese Academy of Sciences [XDB20000000, QYZDY-SSW-SLH012]

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An intermolecular Pd-catalyzed allylic dearomatization reaction of polycyclic indoles with substituted allylic carbonates was realized in the presence of a newly synthesized chiral phosphoramidite ligand. Various polycyclic indoline and indolenine derivatives were successfully synthesized in excellent yields (up to 99%) with excellent enantioselectivity (up to 98% ee). The obtained products could undergo versatile transformations, increasing the application potential of the method in organic synthesis.

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