Determination of the Enantiomeric Excesses of Chiral Acids by 19F NMR Studies of their Esters deriving from (R)-(+)-2-(Trifluoromethyl)benzhydrol
15-Chiral acids were esterified with optically pure (R)-(+)-2-(trifluoromethyl)benzhydrol (R)-(+)-1, a readily available reagent.With respect to the carboxy group, the stereogenic centre is in the β-position in the case of the acids 5a-10a and 12a-16a, and in the α position in the case of the acids 17a-20a.The diastereomeric excesses of the corresponding esters 5b-10b and 12b-20b, respectively, were easily determined by means of 19F NMR.These d.e. values were in very good agreement with the e.e. values of the corresponding acids when the latter were known compounds.
Brown, Eric,Chevalier, Christelle,Huet, Francois,Grumelec, Christelle Le,Leze, Antoine,Touet, Joel
A NEW CHIRAL ACID FOR THE RESOLUTION OF RACEMIC BASES: (S)-(-)-(2-PHENYLCARBAMOYLOXY)PROPIONIC ACID (CARBAMALACTIC ACID).
(S)-(-)-Carbamalactic acid is the phenylcarbamate derived from natural (S)-lactic acid.This new chiral reagent was efficiently used for the resolution of racemic bases such as α-methylbenzylamine, ephedrine and α-(1-naphthyl)ethylamine.