Gold(I)-Catalyzed Tandem 1,2-Indole Migration-Cyclopropanation Reactions of 3-Propargylindoles with Olefins
Lorena Renedo1, Marta Solas1, Raquel Hernández-Ruiz1
1Área de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001, Burgos, Spain.
Abstract:
3-Propargylindoles with a terminal alkyne, efficiently prepared from direct alkylation of indoles, undergo a tandem 1,2-indole migration/cyclopropanation reaction under gold(I) catalysis. Reaction conditions have been developed for suitable access to indole-substituted vinylcyclopropanes from 3-propargyl indoles and olefins. The corresponding 2-alkenyl-functionalized substrates evolve through an intramolecular cyclopropanation allowing the synthesis of various polycyclic indole derivatives. The presence of silver salts modifies the diastereoselectivity observed.
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