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Updated: May 12, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Preparation of tris(spiroorthocarbonate) cyclophanes as back to back ditopic hosts
Hiroshi Danjo1, Kazuhisa Iwaso, Masatoshi Kawahata
1Department of Chemistry and Graduate School of Natural Science, Konan University, 8-9-1 Okamoto, Higashinada, Kobe 658-8501, Japan. danjo@konan-u.ac.jp
Abstract:
Twin-bowl-shaped tris(spiroorthocarbonate) cyclophanes were designed and prepared as ditopic hosts for electrically neutral or electron-rich guests. Preparation of the desired cyclophanes was achieved by cyclotrimerization of 2,2',3,3'-tetrahydroxy-1,1'-binaphthyl (THB) via the transesterification of tetraphenyl orthocarbonate or dichlorodiphenoxymethane. In those reactions, bis(spiroorthocarbonate) cyclophane containing two THB units was also formed as the kinetically favored product. The spiroorthocarbonate twin bowl exhibited ditopic molecular recognition toward fullerene C60 in the crystalline state.
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