Chiral calix[4]arene

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

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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 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.

Original languageEnglish
Pages (from-to)2429-2434
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number10
DOIs
Publication statusPublished - Jan 1 1991

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Shinkai, S., Arimura, T., Kawabata, H., Murakami, H., & Iwamoto, K. (1991). Chiral calix[4]arene. Journal of the Chemical Society, Perkin Transactions 1, (10), 2429-2434. https://doi.org/10.1039/P19910002429