4.8 Article

N-Heterocyclic Carbene (NHC)-Catalyzed Intermolecular Hydroacylation of Cyclopropenes

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 21, Pages 8130-8133

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja202594g

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Funding

  1. Deutscher Akademischer Austausch Dienst
  2. Alfried Krupp von Bohlen und Halbach Foundation

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We report the first intermolecular NHC-catalyzed hydroacylation of electron-neutral olefins. Treatment of aromatic aldehydes with cyclopropenes under mild conditions affords valuable acylcyclopropanes in moderate to high yields with an excellent level of diastereocontrol. Preliminary mechanistic studies suggest that product formation occurs via a concerted syn hydroacylation pathway.

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