High-order dipolar annulations with metal-containing reactive dipoles

Autor: Mao-Mao Zhang, Bao-Le Qu, Bin Shi, Wen-Jing Xiao, Liang-Qiu Lu
Rok vydání: 2022
Předmět:
Zdroj: Chemical Society reviews. 51(10)
ISSN: 1460-4744
Popis: Medium-sized heterocycles are widespread among a spectrum of structurally intriguing and biologically significant natural products and synthetic pharmaceuticals. Metal-catalyzed high-order dipolar annulations resembling reactions of metal-containing reactive dipoles with dipolarophiles constitute a highly efficient and flexible strategy for constructing medium-sized heterocycles. Mechanistically, these annulation reactions usually proceeding through stepwise pathways are different from the classic high-order pericyclic reactions that follow the Woodward-Hoffman rules. More significantly, asymmetric high-order dipolar annulations using chiral organometallic catalysts have been proven successful for constructing chiral medium-sized heterocycles with high enantio- and diastereoselectivity. This review highlights the impressive advances in this area and is focused on the reactivity, scope, mechanisms and applications of high-order dipolar annulation reactions.
Databáze: OpenAIRE