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

Authors
Crucianelli, M Battista, N Bravo, P Volonterio, A Zanda, M
Citation
M. Crucianelli et al., Facile and stereoselective synthesis of non-racemic 3,3,3-trifluoroalanine, MOLECULES, 5(12), 2000, pp. 1251-1258
Citations number
32
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
MOLECULES
ISSN journal
14203049 → ACNP
Volume
5
Issue
12
Year of publication
2000
Pages
1251 - 1258
Database
ISI
SICI code
1420-3049(200012)5:12<1251:FASSON>2.0.ZU;2-K
Abstract
A highly stereoselective enantiodivergent synthesis of non-racemic 3,3,3-tr ifluoroalanine 7 is reported. The methodology is based on the reduction, by 9-BBN or DIBAH, of the chiral sulfinimine 3 derived from ethyl trifluoropy ruvate, followed by acidic hydrolysis of the resulting diastereomeric sulfi namides 4 and 5.