4.8 Article

Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes

Journal

ORGANIC LETTERS
Volume 16, Issue 23, Pages 6196-6199

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol503121q

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Funding

  1. Spanish MINECO [SAF2013-41943-R]
  2. ERDF
  3. European Research Council [340055]
  4. Xunta de Galicia [GRC2013-041]
  5. European Research Council (ERC) [340055] Funding Source: European Research Council (ERC)

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alpha,beta-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields.

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