The mechanism of catalytic enantioselective fluorination: Computational and experimental studies
Piana, Stefano; Devillers, Ingrid; Togni, Antonio; Rothlisberger, Ursula
2002

Abstract

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)]

Details

Title The mechanism of catalytic enantioselective fluorination: Computational and experimental studies
Author(s) Piana, Stefano ; Devillers, Ingrid ; Togni, Antonio ; Rothlisberger, Ursula
Published in Angewandte Chemie, International Edition
Volume 41
Issue 6
Pages 979-982
Date 2002
DOI https://doi.org/10.1002/1521-3773(20020315)41:6<979::AID-ANIE979>3.0.CO;2-E
Laboratories LCBC
Record Appears in Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LCBC - Laboratory of Computational Chemistry and Biochemistry
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date 2006-02-27