Issue 10, 1991
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Chiral calix[4]arene

Seiji Shinkai,   Takashi Arimura,   Hirosuke Kawabata,   Hiroto Murakami  and  Koji Iwamoto  

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.

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Article information

DOI
https://doi.org/10.1039/P19910002429
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1991, 2429-2434

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Chiral calix[4]arene

S. Shinkai, T. Arimura, H. Kawabata, H. Murakami and K. Iwamoto, J. Chem. Soc., Perkin Trans. 1, 1991, 2429 DOI: 10.1039/P19910002429

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