Oxoammonium Salt-Promoted Multifunctionalization of Saturated Cyclic Amines Based On β-Oxo Cyclic Iminium Ion Intermediates
Yan He, Qimeng Liu, Jintao Yang, Zhi Zheng, Guo-Li Chai, Xinying Zhang, Xuesen Fan
Abstract
)-H bond functionalization of saturated cyclic amines through oxoammonium salt-promoted oxidation to afford a β-oxo cyclic iminium ion as a key intermediate, followed by cascade addition with thiocyanate and diverse N-, O-, and S-containing nucleophiles in the green solvent and EtOH. Notably, chiral spiro azapolyheterocycles were prepared enantioselectively (>20:1 dr, up to 99% ee) when cysteine or serine esters were used as substrates. Moreover, the concise late-stage modification of several natural product derivatives was accomplished using this method.
Topics & Concepts
IminiumChemistryThiocyanateSalt (chemistry)NucleophileCyclic aminesSolventCysteineSurface modificationCombinatorial chemistryIonOrganic chemistryMedicinal chemistryCatalysisEnzymePhysical chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques