4.8 Article

Nickel-Catalyzed Chemo- and Enantioselective Coupling between Cyclobutanones and Allenes: Rapid Synthesis of [3.2.2] Bicycles

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 48, Pages 15091-15095

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201609489

Keywords

allenes; C-C activation; cycloaddition; nickel; small ring systems

Funding

  1. NIGMS [R01GM109054]
  2. Welch Foundation [F 1781]

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Herein an intramolecular nickel-catalyzed (4+2) coupling between cyclobutanones and allenes, by C-C cleavage, is reported. The reaction provides a distinct approach for accessing [3.2.2] bicyclic scaffolds which are challenging to prepare through conventional approaches. The reaction is efficient, chemoselective, and pH/redox neutral. Room temperature conditions and low catalyst loadings can be adopted. Excellent enantioselectivity is also achieved.

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