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Facile and Stereoselective Synthesis of Non-Racemic 3,3,3-Trifluoroalanine
Dipartimento di Chimica, Ingegneria Chimica e Materiali, Università di L'Aquila, Via Vetoio, I-67010 Coppito, Italy
Dipartimento di Chimica del Politecnico, via Mancinelli 7, I-20131 Milano, Italy
C.N.R. - Centro di Studio sulle Sostanze Organiche Naturali, via Mancinelli 7, I-20131 Milano, Italy
* Authors to whom correspondence should be addressed.
Received: 6 October 2000; Accepted: 7 November 2000 / Published: 18 December 2000
Abstract: A highly stereoselective enantiodivergent synthesis of non-racemic 3,3,3-trifluoroalanine 7 is reported. The methodology is based on the reduction, by 9-BBN or DIBAH, of the chiral sulfinimine 3 derived from ethyl trifluoropyruvate, followed by acidic hydrolysis of the resulting diastereomeric sulfinamides 4 and 5.
Keywords: Fluorine; Amino acids; Sulfinimines; Asymmetric synthesis
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Crucianelli, M.; Battista, N.; Bravo, P.; Volonterio, A.; Zanda, M. Facile and Stereoselective Synthesis of Non-Racemic 3,3,3-Trifluoroalanine. Molecules 2000, 5, 1251-1258.
Crucianelli M, Battista N, Bravo P, Volonterio A, Zanda M. Facile and Stereoselective Synthesis of Non-Racemic 3,3,3-Trifluoroalanine. Molecules. 2000; 5(12):1251-1258.
Crucianelli, Marcello; Battista, Natalia; Bravo, Pierfrancesco; Volonterio, Alessandro; Zanda, Matteo. 2000. "Facile and Stereoselective Synthesis of Non-Racemic 3,3,3-Trifluoroalanine." Molecules 5, no. 12: 1251-1258.