Metal-Free Catalytic Asymmetric Fluorination of Keto Esters Using a Combination of Hydrogen Fluoride (HF) and Oxidant: Experiment and Computation
KAUST DepartmentPhysical Sciences and Engineering (PSE) Division
Chemical Science Program
KAUST Catalysis Center (KCC)
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AbstractA chiral iodoarene organocatalyst for the catalytic asymmetric fluorination has been developed. The catalyst was used in the asymmetric fluorination of carbonyl compounds, providing the products with a quaternary stereocenter with high enantioselectivities. Chiral hypervalent iodine difluoride intermediates were generated in situ by treatment of the catalyst with an oxidant and hydrogen fluoride as fluoride source. As such, the α-fluorination of a carbonyl compound was achieved with a nucleophilic fluorine source. A combined computational and experimental approach provided insight into the reaction mechanism and the origin of enantioselectivity.
CitationPluta R, Krach PE, Cavallo L, Falivene L, Rueping M (2018) Metal-Free Catalytic Asymmetric Fluorination of Keto Esters Using a Combination of Hydrogen Fluoride (HF) and Oxidant: Experiment and Computation. ACS Catalysis 8: 2582–2588. Available: http://dx.doi.org/10.1021/acscatal.7b03118.
SponsorsP.E.K. thanks the Deutsche Bundesstiftung Umwelt for financial support. We also thank Steven Terhorst and Johannes Baues for technical assistance. L.C. thanks the King Abdullah University of Science and Technology (KAUST) for supporting this work. For computer time, this research used the resources of the KAUST Supercomputing Laboratory (KSL) at KAUST.
PublisherAmerican Chemical Society (ACS)