Nickel-Catalyzed Diastereoselective Cross-Electrophile Ring Opening of 7-Oxabenzonorbornadienes with Aromatic Aldehydes

Abstract

In this protocol, we developed a nickel-catalyzed diastereoselective cross-electrophile ring opening reaction of 7-oxabenzonorbornadienes with aromatic aldehydes as the electrophilic coupling partner utilizing Zn as the stoichiometric reductant. In this reaction, a challenging stereoselective bond formation between two disubstituted sp3-hybridized carbon centers has been achieved, furnishing a variety of 1,2-dihydronaphthalenes with full diastereocontrol of three consecutive stereogenic centers.

Nickel-Catalyzed Cross-Electrophile Ring Opening/gem-Difluoroallylation of Aziridines

“…By circumventing the pregeneration of sensitive organometallics, transition-metal-catalyzed cross-electrophile ring opening (XERO) of cyclic compounds represents an appealing reaction toward C–C bond formation from the viewpoints of step-economy, functional group compatibility, and operational simplicity. , To date, suitable heterocyclic precursors for XERO mainly include epoxides, aziridines, cyclic anhydrides, benzofurans, and heteroatom-bridged bicyclic alkenes . Among them, aziridines are versatile building blocks in organic synthesis, and XERO of such a structural motif with aryl iodides, alkenyl bromides, aldehydes, acetals, CO 2 , or Michael acceptors provides approaches to a variety of amine derivatives (Scheme A).…”