Diastereoselective synthesis of trifluoromethylated gamma-butyrolactones via N-heterocyclic carbene-catalyzed conjugated umpolung of alpha,beta-unsaturated aldehydes
Hirano K, Piel I, Glorius F
Research article (journal)Abstract
The N-heterocyclic carbene-catalyzed conjugate umpolung of differently substituted alpha,beta-unsaturated aldehydes is described. Coupling of these compounds with a variety of trifluoromethylated ketones results in the selective formation of fluorinated gamma-butyrolactones. Using thiazolium-derived N-heterocyclic carbenes, the unlike stereoisomers are formed predominantly, whereas the imidazol-2-ylidene IMes results in lower selectivities and the preferred formation of the like isomer.
Details about the publication
Journal: Advanced Synthesis and Catalysis
Volume: 350
Issue: 7-8
Page range: 984-988
Status: Published
Release year: 2008 (31/05/2008)
Language in which the publication is written: English
Keywords: gamma-butyrolactones N-heterocyclic carbenes organocatalysis organofluorine compounds trifluoromethyl substitution umpolung diels-alder reactions stereoselective-synthesis nucleophilic carbenes direct annulations activated carboxylates enals benzoin generation organocatalysis stereochemistry
Authors from the University of Münster
| Glorius, Frank | Professur für Organische Chemie (Prof. Glorius) |