Atroposelective Construction of Naphthylpyrazoles by Chiral Phosphoric Acid Catalyzed Enantioselective Cross‐Coupling of Pyrazoles with Naphthoquinone Esters
Xi Luo, Sen Li, Yu‐Ting Tian, Yuqi Tian, Limei Gao, Qiang Wang, Qiang Wang, Yongsheng Zheng
Abstract
Abstract The catalytic asymmetric reaction of 5‐aminopyrazoles with naphthoquinone esters has been established. A wide range of unprecedented axially chiral naphthylpyrazole derivatives (29 examples) have been synthesized in moderate to excellent yields (up to 99 % yield) with excellent enantioselectivities (up to 99 % ee) by utilizing chiral phosphoric acid as a catalyst. This protocol features mild reaction conditions, a broad substrate scope, good scalability and facile derivatization. Moreover, preliminary mechanistic investigation was conducted to elucidate the mechanism.
Topics & Concepts
ChemistryPhosphoric acidEnantioselective synthesisCatalysisYield (engineering)Substrate (aquarium)Combinatorial chemistryDerivatizationOrganic chemistryNaphthoquinoneOceanographyHigh-performance liquid chromatographyMaterials scienceGeologyMetallurgyAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralitySphingolipid Metabolism and Signaling