Phosphonium Ylide-Catalyzed <i>Z</i> -Stereoselective Synthesis of α-Substituted Monofluoroalkenes from <i>gem</i> -Difluoroalkenes and Triazoles
Minhui Guan, Yulong Niu, Jiayuan Shui, H. Chen, Lei Wang
Abstract
-difluoroalkenes and triazoles. The reaction is promoted with high stereoselectivity and compatible with a broad range of substrates. A wide range of complex natural products and pharmaceuticals are amenable to late-stage modification. Experimental mechanistic studies indicate that the phosphonium cation, formed via capture of the N-protecting group of triazole by the phosphine ylide, may play a key role in governing stereoselectivity.
Topics & Concepts
PhosphoniumChemistryPhosphineCombinatorial chemistryYlideStereoselectivityCatalysisOrganic chemistrySurface modificationTotal synthesisTriazoleOrganocatalysisReaction conditionsOrganic synthesisRange (aeronautics)Functional groupStereoisomerismFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsClick Chemistry and Applications