Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 127, Issue 7, Pages 930-935Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2006.04.004
Keywords
1,3-proton shift reaction; fluorine and compounds; imines; enamines; operationally convenient conditions; asymmetric synthesis; biomimetic reductive methodology
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An asymmetric synthesis of (S)- and (R)-3-amino-4,4,4-trifluorobutanoic acid via DBU-catalyzed asymmetric 1,3-proton shift transfer reaction of (Z)-3-[(R)-1-phenylethylaminol-4,4,4-trifluoro-N-[(R)-1-phenylethyl]but-2-enamide has been developed. The intermediate Schiff base (S,R')-9 was found to be relatively configurationally stable under the highly basic reaction conditions allowing preparation of the target amino acid in high chemical yield and enantioselectivity. This method was demonstrated to be practical for large (> 25 g) scale synthesis of the target beta-amino acid. (c) 2006 Elsevier B.V. All rights reserved.
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