4.8 Article

Enantioselective Synthesis of Highly Substituted Furans by a Copper(II)-Catalyzed Cycloisomerization-Indole Addition Reaction

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 22, Pages 8486-8489

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja202959n

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Funding

  1. Office of Science of the U.S. Department of Energy [DE-AC02-05CH11231]
  2. NSERC
  3. Hertz Foundation

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A catalytic enantioselective reaction based on a copper(II) catalyst strictly containing chiral anionic ligands is described. In the present work, copper(II)-phosphate catalyst promotes the intramolecular heterocyclization of 2-(1-alkynyl)-2-alkene-1-ones and facilitates high levels of enantioselectivity in the subsequent nucleophile attack. Mechanistic studies suggest that formation of a copper(II)-indole species is important for catalysis.

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