The mechanism of catalytic enantioselective fluorination: Computational and experimental studies
A parallel orientation between the coordinated substrate enolate and a face-on naphthyl group of the TAD-DOL ligand control the stereochem. outcome of the Ti-catalyzed asym. fluorination of 1,3-dicarbonyl compds. with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octanetriethylenediamine (F-TEDA). D. functional theory based quantum-mech. mol. mech. calcns. also disclose the fluorine-transfer step as occurring by a single-electron transfer. [on SciFinder (R)]
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Piana, S., Devillers, I., Togni, A., & Rothlisberger, U. (2002). The mechanism of catalytic enantioselective fluorination: Computational and experimental studies. Angewandte Chemie International Edition, 41(6), 979–982. https://doi.org/10.1002/1521-3773(20020315)41:6<979::AID-ANIE979>3.0.CO;2-E
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2002
41
6
979
982
REVIEWED
EPFL