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Gold‐Catalyzed Bicyclic Annulations of 2‐Alkynylbenzaldehydes with Vinyldiazo Carbonyls that Serve as Five‐atom Building Units
Author(s) -
Raj Antony Sekar Kulandai,
Liu RaiShung
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201905350
Subject(s) - bicyclic molecule , catalysis , stereoselectivity , chemistry , atom (system on chip) , molecule , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , computer science , embedded system
This work reports gold‐catalyzed bicyclic annulations of 2‐alkynyl‐1‐carbonylbenzenes with vinyldiazo ketones that serve as five‐atom building units. The importance of these reactions is to access 4,5‐dihydro‐benzo[ g ]indazoles, which form the structural cores of various bioactive molecules. According to our mechanistic analysis, we postulate initial [5+4]‐cycloadditions between benzopyrilium intermediates and vinyldiazo ketones, followed by 6‐π‐electrocyclizations to achieve the excellent stereoselectivity.