Synthesis of Planar-Chiral [2.2]Paracyclophane-based Oxazole-Pyrimidine Ligands and Application in Nickel-Catalyzed 1,2-Reduction of α,β-Unsaturated Ketones Juan Wang, Qing-Xian Xie, Xiang Li, Chang-Bin Yu,* and Yong-Gui Zhou* Chin. J. Chem.2023, 41, XXX—XXX. DOI: 10.1002/cjoc.202300XXX
The [2.2]paracyclophane-derived oxazole-pyrimidine ligands with planar chirality (PYMCOX) were designed, synthesized and successfully applied in nickel-catalyzed asymmetric 1,2-reduction of α,β-unsaturated ketones, affording the chiral allyilic alcohols with up to 99% yield and 99% ee. Meanwhile, this reduction reaction could be conducted on gram scale without loss of activity and enantioseletivity, and the chiral ligand could be conveniently recovered with high yield.