Chiral calix[4]arene
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- Vol. 23 (10) , 2429-2434
- https://doi.org/10.1039/p19910002429
Abstract
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 ringoriginating 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.Keywords
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