145029-02-3Relevant academic research and scientific papers
Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization
Biosca, Maria,Eriksson, Lars,Hedberg, Martin,Himo, Fahmi,Lübcke, Marvin,Szabó, Kálmán J.,Wang, Qiang
, p. 20048 - 20057 (2020)
1,1-Disubstituted styrenes with internal oxygen and nitrogen nucleophiles undergo oxidative fluorocyclization reactions with in situ generated chiral iodine(III)-catalysts. The resulting fluorinated tetrahydrofurans and pyrrolidines contain a tertiary carbon-fluorine stereocenter. Application of a new 1-naphthyllactic acid-based iodine(III)-catalyst allows the control of tertiary carbon-fluorine stereocenters with up to 96% ee. Density functional theory calculations are performed to investigate the details of the mechanism and the factors governing the stereoselectivity of the reaction.
