Enantioselective Synthesis of α-All-Carbon Quaternary Center-Containing Carbazolones via Amino-palladation/Desymmetrizing Nitrile Addition Cascade
Xudong Hu, Zi‐Hao Chen, Jing Zhao, Ruize Sun, Hui Zhang, Xiaotian Qi, Wen‐Bo Liu
Abstract
An enantioselective Pd(II)-catalyzed amino-cyclization and desymmetrizing nitrile addition cascade reaction of alkyne-tethered malononitriles is reported. This reaction forms two rings and one quaternary carbon center in a single step and serves as an efficient strategy for the construction of α-quaternary carbazolones with high enantioselectivities (up to 98:2 er). The utility of this method is demonstrated by product derivatization into a diverse array of heterocycles and a nitrile-containing leucomidine A analog.
Topics & Concepts
ChemistryNitrileEnantioselective synthesisAlkyneQuaternary carbonCascadeDerivatizationCombinatorial chemistryCascade reactionCatalysisOrganic chemistryHigh-performance liquid chromatographyChromatographyCatalytic C–H Functionalization MethodsAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods