Gold(I)‐Catalyzed Carboaminations of Allenes by N‐Allyltetrahydro‐β‐carbolines: An Experimental and Theoretical Study

作者: Valérian Gobé , Maxime Dousset , Pascal Retailleau , Vincent Gandon , Xavier Guinchard

DOI: 10.1002/ADSC.201601075

关键词: AlleneCatalysisCope rearrangementMoietyHomogeneous catalysisIsomerizationDensity functional theoryAntarafacial and suprafacialChemistryStereochemistry

摘要: N-Allyltetrahydro-β-carbolines bearing a pendant allene undergo unprecedented gold(I)-catalyzed cyclizations proceeding with an allyl migration from the nitrogen to moiety. The initial product of gold-catalyzed cyclization evolves either via isomerization or Cope rearrangement, leading different scaffolds. Density function theory (DFT) calculations established that occurs in asynchronous suprafacial manner.

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