2024
DOI: 10.1021/acs.orglett.4c03709
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Chiral Biaryl N-Heterocyclic Carbene–Palladium Catalysts with Anagostic C–H···Pd Interaction for Enantioselective Desymmetric C–N Cross-Coupling

Woosong Han,
Huijeong Ryu,
Changmuk Kang
et al.

Abstract: Novel chiral biaryl imidazo[1,5-a]pyridine carbene− palladium complexes (ImPy−Pd) featuring an anagostic C−H•••Pd interaction and a C5-aryl substituent have been developed and successfully applied to the Pd-catalyzed enantioselective desymmetric C−N cross-coupling of malonamide derivatives, providing chiral 3,4-dihydroquinoline-2-ones with quaternary stereocenters in high yields (≤99%) and enantioselectivities (≤97:3 er). The chiral catalyst exerts stereocontrol by restricting the rotation of substituents arou… Show more

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