4.8 Article

Enantioselective Intramolecular Hydroacylation of Unactivated Alkenes: An NHC-Catalyzed Robust and Versatile Formation of Cyclic Chiral Ketones

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 42, Pages 12492-12496

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201412302

Keywords

enantioselective catalysis; hydroacylation; N-heterocyclic carbenes; organocatalysis

Funding

  1. Fonds der Chemischen Industrie
  2. Deutsche Forschungsgemeinschaft [SPP 1179, IRTG 2027]

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A highly enantioselective intramolecular N-heterocyclic carbene (NHC)-catalyzed hydroacylation reaction gives access to a range of cyclic ketones from unactivated olefin-substituted aldehydes (up to 99% ee). Remarkably, aliphatic aldehydes were also transformed efficiently in an NHC-catalyzed hydroacylation reaction for the first time.

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