Determination of the enantiomeric purity and the configuration of β-aminoalcohols using (R)-2-fluorophenylacetic acid (AFPA) and fluorine-19 NMR: application to β- …

…, YB Tiba, PM Léo, S Hamman, C Coulombeau

Index: Apparu, Marcel; Ben Tiba, Younes; Leo, Pierre-Marc; Hamman, Sylvain; Coulombeau, Christian Tetrahedron Asymmetry, 2000 , vol. 11, # 14 p. 2885 - 2898

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Citation Number: 21

Abstract

A method has been developed for determining the enantiomeric purity and the absolute configuration of β-aminoalcohols of type ArOCH2CH (OH) CH2NHR (R= iPr, tBu). To determine enantiomeric purity, the amine function was first protected by a benzyl group, then the compound formed was esterified using the acid chloride of (R)-2-fluorophenylacetic acid (AFPA). The 19F NMR analysis of the derivative obtained revealed the presence of two ...