Facile and Stereoselective Synthesis of Non-Racemic 3,3,3-TrifluoroalanineReport as inadecuate


Facile and Stereoselective Synthesis of Non-Racemic 3,3,3-Trifluoroalanine


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1

Dipartimento di Chimica, Ingegneria Chimica e Materiali, Università di LAquila, Via Vetoio, I-67010 Coppito, Italy

2

Dipartimento di Chimica del Politecnico, via Mancinelli 7, I-20131 Milano, Italy

3

C.N.R. - Centro di Studio sulle Sostanze Organiche Naturali, via Mancinelli 7, I-20131 Milano, Italy





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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. View Full-Text

Keywords: Fluorine; Amino acids; Sulfinimines; Asymmetric synthesis Fluorine; Amino acids; Sulfinimines; Asymmetric synthesis





Author: Marcello Crucianelli 1,*, Natalia Battista 1, Pierfrancesco Bravo 2,3, Alessandro Volonterio 2 and Matteo Zanda 2,*

Source: http://mdpi.com/



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