Transition metal-catalyzed dipolar cycloadditions have been established as a powerful tool for constructing valuable heterocyclic skeletons. Though important advances in this field, the construction of heterocycles bearing quaternary stereocenters and medium-sized rings with high enantio- and chemo-selectivities has not yet been well developed. In the past years, we have developed a kind of chiral hybrid P,S ligands starting from commercially available chiral 2-amino-1,2-diphenylethanols. They exhibit great performance on the palladium-catalyzed asymmetric [4+2]1, [5+2]2a, [6+2]2b and [8+2]2c dipolar cycloadditions, as well as the copper-catalyzed [3+2]3 cycloadditions. A variety of chiral aza- and oxo-heterocyclic products bearing challenging quaternary stereocenters and medium-sized rings can be prepared in generally good yields and with high enantioselectivities. Moreover, mechanism studies with X-ray single crystal diffraction, 2D NMR, HRMS and DFT calculations were performed to illustrate the stereoinduction of these chiral P,S ligands.

Chiral P,S Ligands: Privileged Ligands in Metal-Catalyzed Asymmetric Dipolar Cycloadditions

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