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Determination of the enantiomeric excesses of chiral acids by 19F NMR studies of their esters deriving from (R)-(+)-2-(trifluoromethyl)benzhydrol

Authors :
Christelle Le Grumelec
Joël Touet
Christelle Chevalier
Eric Brown
Antoine Lézé
François Huet
Source :
Tetrahedron: Asymmetry. 5:1191-1194
Publication Year :
1994
Publisher :
Elsevier BV, 1994.

Abstract

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 19 F 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.

Details

ISSN :
09574166
Volume :
5
Database :
OpenAIRE
Journal :
Tetrahedron: Asymmetry
Accession number :
edsair.doi...........bfa8f589853a0eb6ecd56d1231baf42c
Full Text :
https://doi.org/10.1016/0957-4166(94)80154-1