A cone-shaped, asymmetrically substituted p-tert-butylcalixarene 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-butylcalixarene. 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 calixarene.
|Number of pages||6|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|Publication status||Published - Jan 1 1991|
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