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- Title
Fluorinated Organocatalysts for the Enantioselective Epoxidation of Enals: Molecular Preorganisation by the Fluorine-Iminium Ion Gauche Effect.
- Authors
Tanzer, Eva-Maria; Zimmer, Lucie E.; Schweizer, W. Bernd; Gilmour, Ryan
- Abstract
The fluorine-iminium ion gauche effect is triggered upon union of a secondary β-fluoroamine and an α,β-unsaturated aldehyde, providing a useful strategy for controlling the molecular topology of intermediates that are central to organocatalytic processes. The β-fluoroamine ( S)-2-(fluorodiphenylmethyl)pyrrolidine ( 1) is an effective catalyst for the enantioselective epoxidation of α,β-unsaturated aldehydes. A process of structural editing has revealed that the efficiency of this catalyst is due to the (fluorodiphenyl)methyl group when it is embedded in a β-fluoroiminium motif. Epoxidations of challenging cyclic α,β-disubstituted, β,β-disubstituted and α,β,β-trisubstituted enals catalysed by 1 proceed with excellent levels of enantiocontrol (up to 98 % ee).
- Publication
Chemistry - A European Journal, 2012, Vol 18, Issue 36, p11334
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201201316