TY - JOUR
T1 - Chiral calix[4]arene
AU - Shinkai, Seiji
AU - Arimura, Takashi
AU - Kawabata, Hirosuke
AU - Murakami, Hiroto
AU - Iwamoto, Koji
PY - 1991/1/1
Y1 - 1991/1/1
N2 - A cone-shaped, asymmetrically substituted p-tert-butylcalix[4]arene has been synthesized and optically resolved. The oxygen-through-the-annulus rotation which causes racemization of these ring- originating optical isomers is suppressed by four O-propyl substituents. In the synthesis the use of Ba(OH)2 as the base for the O-propylation is a key point: it affords only a cone-shaped, conformationally immobile tri-O-propylated p-tert-butylcalix[4]arene. After O-substitution with the fourth propyl group, the racemic product can be optically resolved by HPLC. This is the first example of a successful optical resolution of an asymmetrically substituted calix[4]arene.
AB - A cone-shaped, asymmetrically substituted p-tert-butylcalix[4]arene has been synthesized and optically resolved. The oxygen-through-the-annulus rotation which causes racemization of these ring- originating optical isomers is suppressed by four O-propyl substituents. In the synthesis the use of Ba(OH)2 as the base for the O-propylation is a key point: it affords only a cone-shaped, conformationally immobile tri-O-propylated p-tert-butylcalix[4]arene. After O-substitution with the fourth propyl group, the racemic product can be optically resolved by HPLC. This is the first example of a successful optical resolution of an asymmetrically substituted calix[4]arene.
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U2 - 10.1039/P19910002429
DO - 10.1039/P19910002429
M3 - Article
AN - SCOPUS:37049075660
SN - 1472-7781
SP - 2429
EP - 2434
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
IS - 10
ER -