Facile and stereoselective synthesis of non-racemic 3,3,3-trifluoroalanine

Molecules

Volumn 5, Issue 12, 2000, Pages 1251-1258

  Crucianelli, Marcello ^a   Battista, Natalia ^a   Bravo, Pierfrancesco ^b,c   Volonterio, Alessandro ^b   Zanda, Matteo ^b  

^a UNIVERSITY OF L'AQUILA   (Italy)

^b POLITECNICO DI MILANO   (Italy)

^c CNR   (Italy)

Author keywords

Amino acids; Asymmetric synthesis; Fluorine; Sulfinimines

Indexed keywords

3,3,3 TRIFLUORALANINE; ALANINE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHIRALITY; CONFERENCE PAPER; DIASTEREOISOMER; ENANTIOMER; HYDROLYSIS KINETICS; ORGANIC CHEMISTRY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0008631779     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/51201251     Document Type: Conference Paper

References (38)

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33. A similar side-reaction has been observed for related fluorine-containing compounds: see Ref. 7b.
34. (a) Asensio, A.; Bravo, P.; Crucianelli, M.; Farina, A.; Fustero, S.; Soler, J. C.; Meille, S. V.; Panzeri, W.; Viani, F.; Volonterio, A.; Zanda, M. submitted for publication.
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38. In our hands, free 3,3,3-trifluoroalanine 7 was poorly stable. We observed complete decomposition of solid samples of 7, purified by ion-exchange chromatography, after one week at 4 °C. Racemic 7 is known to undergo progressive elimination of HF at pH > 6: Weygand, F.; Steglich, W.; Oettmeier, W. Chem. Ber. 1970, 103, 1655-1663. Therefore, we cannot rule out that a partial racemization of free 7 might take place during the purification or storage, even if short.