4.8 Article

Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 39, Pages 13614-13617

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja508523g

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Funding

  1. National Institutes of Health [GM-099920, GM-43214]
  2. NSERC
  3. Vertex Pharmaceuticals, Inc.
  4. NIH [GM-067041]

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We report the development of a catalytic method for the enantioselective addition of indoles to pyrone-derived electrophiles. Arylpyrrolidino-derived thioureas catalyze the addition with high stereoselectivity in the presence of catalytic quantities of an achiral Bronsted acid. The indole-pyrone adducts feature a quaternary stereocenter and represent an unusual class of indolines bearing structural resemblance to the hybrid natural product pleiocarpamine.

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