Nickel-Catalyzed, Enantioselective Hydrofluoromethylation of Olefins: Access to Chiral α-Fluoromethylated Amides and Esters
Yiming Du, Shuxin Chen, Hexiang Cao, Yichen Zhang, Hongtao Lei, Guoqin Xia, Huicai Huang, Zhaodong Li
Abstract
We herein report the nickel-catalyzed enantioselective hydrofluoromethylation of enamides and enol esters with CH 2 FI as the fluoromethyl source to enable the diversity-oriented synthesis (DOS) of chiral α-fluoromethylated amides as well as esters with features of wide functional group compatibility as well as excellent enantioselectivity. The synthetic value of this protocol was demonstrated by transformations of the resulted α-fluoromethylated amides to different scaffolds including amine, oxazoline, thiazoline, and α-fluoromethylated tetrahydroquinoline.
Topics & Concepts
Enantioselective synthesisChemistryCatalysisOxazolineAmine gas treatingNickelEnolCombinatorial chemistryStereoisomerismOrganic chemistryAmideFluorine in Organic ChemistryCyclopropane Reaction MechanismsCarbon dioxide utilization in catalysis