Bulky alkali metal cations enabled highly efficient iridium-catalyzed asymmetric hydrogenation for C–N axial chirality via dynamic kinetic resolution

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dynamic kinetic resolution under mild conditions, allowing for the construction of axial chirality with excellent stereocontrol (up to >99% ee and >99 : 1 dr). DFT studies indicate that strong electrostatic interaction between the bulky cesium cation and the oxygen atom of the substrate dramatically reduces the activation barrier, resulting in a substantially accelerated reaction rate for the anionic Ir catalyst (HIr-NCs) compared to the neutral Ir/Huaphos system (HIr-NH). In the presence of anionic Ir catalyst, this protocol can be scaled up to gram quantities under an exceptionally low catalyst loading (S/C = 40 000), and the resulting hydrogenation product can be further transformed into novel chiral ligands that show promise in asymmetric catalysis.

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