RESOLUTION OF INHERENTLY CHIRAL 1,4-2,5-CALIX[8]BIS-CROWN-4 DERIVATIVES BY ENANTIOSELECTIVE HPLC

Authors
CACCAMESE S PRINCIPATO G GERACI C NERI P
Citation
S. Caccamese et al., RESOLUTION OF INHERENTLY CHIRAL 1,4-2,5-CALIX[8]BIS-CROWN-4 DERIVATIVES BY ENANTIOSELECTIVE HPLC, Tetrahedron : asymmetry, 8(8), 1997, pp. 1169-1173
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
8
Year of publication
1997
Pages
1169 - 1173
Database
ISI
SICI code
0957-4166(1997)8:8<1169:ROIC1D>2.0.ZU;2-B
Abstract
The first example of the resolution of inherently chiral calix[8]arene s, 1,4-2,5-calix[8]bis-crown-4 1 and its methyl derivatives 2-4, has b een achieved using enantioselective HPLC methods. The enantiomeric nat ure of isolated (+)-1 and (-)-1 was confirmed by CD spectra, specific optical rotation and H-1 NMR in the presence of Pirkle's reagent. A ra tionale is given for the observed HPLC enantioselectivity among compou nds 2-4. (C) 1997 Elsevier Science Ltd.