Operationally convenient asymmetric synthesis of (S)- and (R)-3-amino-4,4,4-trifluorobutanoic acid
In: Journal of Fluorine Chemistry, Jg. 127 (2006-07-01), S. 930-935
Online
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Zugriff:
DBU-catalyzed asymmetric synthesis of (S)- and (R)-3-amino-4,4,4-trifluorobutanoic acid via enantioselective biomimetic transamination of isopropyl 4,4,4-trifluoro-3-oxobutanoate with (R)- and (S)-phenylethylamine has been developed. The effect of the base concentration of the reaction rate and stereochemical outcome has been systematically studied. The key reaction step, DBU-catalyzed 1,3-proton shift transfer was found to be highly enantioselective (>95% ee). However, due to some racemization of the intermediate Schiff base under the highly basic reaction conditions leads to the final product of lower enantiomeric purity.
Titel: |
Operationally convenient asymmetric synthesis of (S)- and (R)-3-amino-4,4,4-trifluorobutanoic acid
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Autor/in / Beteiligte Person: | Soloshonok, Vadim A. ; Yasumoto, Manabu ; Ohkura, Hironari |
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Zeitschrift: | Journal of Fluorine Chemistry, Jg. 127 (2006-07-01), S. 930-935 |
Veröffentlichung: | Elsevier BV, 2006 |
Medientyp: | unknown |
ISSN: | 0022-1139 (print) |
DOI: | 10.1016/j.jfluchem.2006.04.004 |
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