Rhodium‐Catalyzed Enantio‐ and Regioselective Allylation of Indoles with <i>gem</i> ‐Difluorinated Cyclopropanes
Hui Yang, Yaxin Zeng, Xiangyu Song, Lin Che, Zhong‐Tao Jiang, Gang Lü, Ying Xia
Abstract
The use of gem-difluorinated cyclopropanes (gem-DFCPs) as fluoroallyl surrogates under transition-metal catalysis has drawn considerable attention recently but such reactions are restricted to producing achiral or racemic mono-fluoroalkenes. Herein, we report the first enantioselective allylation of indoles under rhodium catalysis with gem-DFCPs. This reaction shows exceptional branched regioselectivity towards rhodium catalysis with gem-DFCPs, which provides an efficient route to enantioenriched fluoroallylated indoles with wide substrate scope and good functional group tolerance.
Topics & Concepts
RegioselectivityRhodiumCatalysisEnantioselective synthesisChemistryCombinatorial chemistryOrganic chemistryFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods