Gold‐Catalyzed Bicyclic Annulations of 2‐Alkynylbenzaldehydes with Vinyldiazo Carbonyls that Serve as Five‐atom Building Units

作者: Antony Sekar Kulandai Raj , Rai‐Shung Liu

DOI: 10.1002/ANIE.201905350

关键词: CatalysisBioactive moleculesStereoselectivityChemistryBicyclic moleculeComputational chemistryAtom (order theory)

摘要: This work reports gold-catalyzed bicyclic annulations of 2-alkynyl-1-carbonylbenzenes with vinyldiazo ketones that serve as five-atom building units. The importance these reactions is to access 4,5-dihydro-benzo[g]indazoles, which form the structural cores various bioactive molecules. According our mechanistic analysis, we postulate initial [5+4]-cycloadditions between benzopyrilium intermediates and ketones, followed by 6-π-electrocyclizations achieve excellent stereoselectivity.

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