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NiH-Catalyzed Regio- and Enantioselective Hydroalkylation for the Synthesis of β- or γ-Branched Chiral Aromatic N-Heterocycles

Ju‐Song Yang, Ka Lu, Chen‐Xiao Li, Zu‐Hang Zhao, Fu‐Min Zhang, Xiao‐Ming Zhang, Yong‐Qiang Tu

2023Journal of the American Chemical Society30 citationsDOI

Abstract

A nickel hydride-catalyzed regio- and enantioselective hydroalkylation reaction was developed to give access to a library of chiral β- or γ-branched aromatic N-heterocycles. This intriguing asymmetric transformation features excellent selectivities, step- and atom-economies, and generating two kinds of chiral products through one synthetic strategy. Furthermore, the possible reaction mechanism was extensively investigated using numerous control experiments and density functional theory calculations.

Topics & Concepts

Enantioselective synthesisChemistryCatalysisHydrideCombinatorial chemistryOrganic chemistryMetalCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis
NiH-Catalyzed Regio- and Enantioselective Hydroalkylation for the Synthesis of β- or γ-Branched Chiral Aromatic N-Heterocycles | Litcius