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

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 sulfi...

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Bibliographic Details
Published in:MolBank 2000-12, Vol.5 (12), p.1251-1258
Main Authors: Crucianelli, Marcello, Battista, Natalia, Bravo, Pierfrancesco, Volonterio, Alessandro, Zanda, Matteo
Format: Article
Language:English
Subjects:
Amino acids
Asymmetric synthesis
Fluorine
Sulfinimines
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Summary: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.
ISSN:1420-3049
1420-3049
1422-8599
DOI:10.3390/51201251