4.8 Article

Chiral Diphosphine-Palladium-Catalyzed Sequential Asymmetric Double-Friedel-Crafts Alkylation and N-Hemiketalization for Spiropolycyclic Indole Derivatives

Journal

ORGANIC LETTERS
Volume 19, Issue 8, Pages 1954-1957

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00368

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Funding

  1. National Natural Science Foundation of China [21572150]
  2. Natural Science Foundation of the Jiangsu Higher Education Institutions [13KJA150004]
  3. Program for New Century Excellent Talents in University [NCET-12-0743]
  4. Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)

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An efficient cascade asymmetric Friedel-Crafts alkylation/N-hemiketalization/Friedel-Crafts alkylation reaction of 3-alkylindoles with oxindolyl beta,gamma-unsaturated a-ketoesters has been developed in the presence of a chiral diphosphine-palladium(II) catalyst. A series of enantiomerically enriched spiro-polycyclic indole derivatives have been constructed in high yields with excellent enantioselectivities and diastereoselectivities.

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