Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization
Qiang Wang, Marvin Lübcke, Maria Biosca, M. Hedberg, Lars Eriksson, Fahmi Himo, Kálmán J. Szabó
Abstract
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.
Topics & Concepts
StereocenterChemistryEnantioselective synthesisNucleophileFluorineCatalysisOrganocatalysisStereoselectivityCarbon fibersOrganic chemistryFluorideCombinatorial chemistryInorganic chemistryComposite materialMaterials scienceComposite numberFluorine in Organic ChemistryOxidative Organic Chemistry ReactionsAsymmetric Synthesis and Catalysis