Gold(I)-Catalyzed Tandem 1,2-Indole Migration-Cyclopropanation Reactions of 3-Propargylindoles with Olefins.

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.

SUBMITTER: Renedo L 

PROVIDER: S-EPMC12340974 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature