Synthesis and chiroptical properties of cylindrical macrocycles comprising two calix[3]aramide moieties

Yuuki Saito; Misa Satake; Ryuichi Mori; Misaki Okayasu; Hyuma Masu; Masahide Tominaga; Kosuke Katagiri; Kentaro Yamaguchi; Shoko Kikkawa; Hidemasa Hikawa; Isao Azumaya

doi:10.1039/C9OB02022E

Synthesis and chiroptical properties of cylindrical macrocycles comprising two calix[3]aramide moieties†

Yuuki Saito,^a Misa Satake,^a Ryuichi Mori,^a Misaki Okayasu,

^a Hyuma Masu,

^b Masahide Tominaga,

^c Kosuke Katagiri,

^d Kentaro Yamaguchi,

^c Shoko Kikkawa,

^a Hidemasa Hikawa

^a and Isao Azumaya

*^a

Author affiliations

* Corresponding authors

^a Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan
E-mail: isao.azumaya@phar.toho-u.ac.jp

^b Center for Analytical Instrumentation, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

^c Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan

^d Department of Chemistry, Faculty of Science and Engineering, Konan University, 8-9-1 Okamoto, Higashinada-ku, Kobe, Hyogo 658-8501, Japan

Abstract

Calix[3]aramide-based cylindrical macrocycles were synthesized by the one-step amide coupling reaction of a monomer containing two meta-alkylaminobenzoic acid units linked by para-phenylene bridges. The major products included a meso-form and an enantiomeric pair, with stereochemistry derived from the direction of the amide bonds and their fixed conformation. Mirror-image ECD, VCD, and CPL spectra were observed in the enantiomeric pair and the absolute structure was determined by comparing measured and calculated ECD and VCD spectra.

This article is part of the themed collection: Supramolecular chemistry in OBC

Organic & Biomolecular Chemistry

Synthesis and chiroptical properties of cylindrical macrocycles comprising two calix[3]aramide moieties†

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Synthesis and chiroptical properties of cylindrical macrocycles comprising two calix[3]aramide moieties

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