Chiral calix[4]arene

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

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)


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
Publication statusPublished - 1991
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • General Chemistry


Dive into the research topics of 'Chiral calix[4]arene'. Together they form a unique fingerprint.

Cite this