Catalytic asymmetric defluorinative allylation of silyl enol ethers
Jordi Duran, Javier Mateos, Albert Moyano, Xavier Companyó
Abstract
a Si-F interaction. A series of spectroscopic, electroanalytic and kinetic experiments demonstrate the crucial interplay of the Si-F interaction for successful reactivity and selectivity. The generality of the transformation is demonstrated by synthesising a wide set of structurally diverse α-allylated ketones bearing two contiguous stereocenters. Remarkably, the catalytic protocol is amenable for the allylation of biologically significant natural products.
Topics & Concepts
ChemistryStereocenterSilylationEnolNucleophileEnantioselective synthesisCatalysisReactivity (psychology)AlkylKinetic resolutionStereochemistryCombinatorial chemistryOrganic chemistryPathologyAlternative medicineMedicineFluorine in Organic ChemistryAsymmetric Synthesis and CatalysisRadical Photochemical Reactions