Bifunctinoal Phosphonium Salt‐Catalyzed Asymmetric Cyclodearomatization of 2‐Nitroindoles and 2‐Nitrobenzofurans for Constructing CF<sub>3</sub>‐Containing Spiro‐Polycycles
Zhiyu Jiang, Xin Liu, Hongkui Zhang, Jian‐Ping Tan, Xiaoyu Ren, Guowei Gao, Tianli Wang
Abstract
Abstract An efficient enantioselective dearomative cycloaddition reaction between either 2‐nitroindoles or 2‐nitrobenzofurans and N ‐2,2,2‐trifluoroethylisatin ketimines by dipeptided phosphonium salt catalysis is firstly established. This protocol provides a new and facile synthetic approach to create a variety of CF 3 ‐containing polycyclic spirooxindole derivatives under mild reaction conditions with high yields in excellent diastereo‐ and enantioselectivities (all >20:1 dr , up to 95% ee). magnified image
Topics & Concepts
ChemistryEnantioselective synthesisPhosphoniumSalt (chemistry)CycloadditionCatalysisPhosphonium saltCombinatorial chemistryReaction conditionsOrganocatalysisOrganic chemistryMedicinal chemistryFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods