A NEW STEREOCHEMICAL MODEL FROM NMR FOR BENZOYLATED CYCLODEXTRINS, PROMISING NEW CHIRAL SOLVATING AGENTS FOR THE CHIRAL ANALYSIS OF 3,5-DINITROPHENYL DERIVATIVES

Authors
UCCELLOBARRETTA G CUZZOLA A BALZANO F MENICAGLI R IULIANO A SALVADORI P
Citation
G. Uccellobarretta et al., A NEW STEREOCHEMICAL MODEL FROM NMR FOR BENZOYLATED CYCLODEXTRINS, PROMISING NEW CHIRAL SOLVATING AGENTS FOR THE CHIRAL ANALYSIS OF 3,5-DINITROPHENYL DERIVATIVES, Journal of organic chemistry, 62(4), 1997, pp. 827-835
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
4
Year of publication
1997
Pages
827 - 835
Database
ISI
SICI code
0022-3263(1997)62:4<827:ANSMFN>2.0.ZU;2-Z
Abstract
Hexakis(2,3-di-O-benzoyl)-alpha-cyclodextrin and hexakis(2,3,6-tri-O-b enzoyl)-alpha-cyclodextrin have been employed as chiral solvating agen ts (CSAs) for the NMR determination of the enantiomeric composition of derivatives of chiral amines, amino alcohols, alcohols, carboxyl acid s, and amino acids bearing a 3,5-dinitrophenyl moiety. The conformatio nal features of the two cyclodextrins have been carefully analyzed by NMR spectroscopy, and the origin of the symmetry change (C-6 --> C-3), detected by NMR for hexakis(2,3-di-O-benzoyl)-alpha-cyclodextrin in C DCl3, has been clarified.