4.8 Article

Palladium(II)/Bronsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 20, Pages 6024-6027

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201501048

Keywords

carbocyclization; chiral anion; chiral phosphoric acid; oxidation; palladium

Funding

  1. European Research Council (ERC) [AdG 247014]
  2. Swedish Research Council [621-2013-4653]
  3. Berzelii Centre EXSELENT
  4. Knut and Alice Wallenberg Foundation

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An enantioselective oxidative carbocyclization-borylation of enallenes that is catalyzed by palladium(II) and a Bronsted acid was developed. Biphenol-type chiral phosphoric acids were superior co-catalysts for inducing the enantioselective cyclization. A number of chiral borylated carbocycles were synthesized in high enantiomeric excess.

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