Enantioselective organocatalytic route to trifluoromethyl-β-amino acids using chiral bases |
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Authors: | Valé rie Michaut,Jean-Marc Paris,Jean-Christophe Plaquevent |
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Affiliation: | a UMR-CNRS 6014, IRCOF, Université de Rouen, rue Tesnière, F-76821 Mont-Saint-Aignan Cedex, France b Rhodia Recherches, Centre de Recherches de Lyon, 85 avenue des Frères Perret F-69192 Saint-Fons, France |
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Abstract: | Herein are studied new aspects of enantioselective (1,3) proton transfer of ethyl-4,4,4-trifluoroacetoacetate (ETFAA) amino derivatives. When catalyzed by an appropriate chiral base, ee's as high as 71% are observed. Special emphasis is given to mechanistic insights of the reaction by use of deuterated derivative. All results converge on a deprotonation as both rate and asymmetric determining step. This study opens a new route to trifluoromethylated chiral building blocks. |
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Keywords: | Trifluoromethyl compounds β-Amino acids and derivatives Chiral bases Proton shift transfer reaction Asymmetric synthesis |
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