title: Control of a Chiral Property of a Calix[3]aramide: The Racemization Suppressed by Intramolecular Cyclic Hydrogen Bonds and DMSO-H2O System-Induced Spontaneous Resolution.
abstract: A calix[3]aramide has been synthesized bearing three triphenylphosphinic amide moieties, which formed intramolecular cyclic hydrogen bonds that suppressed its cone/partial cone inversion. The intramolecular cyclic hydrogen bonds were disrupted by DMSO, and the insertion of H2O into the hydrogen bonds triggered the spontaneous resolution of the calix[3]aramide. Within a chiral environment, such as that afforded by the presence of optically active 2-butanol, the calix[3]aramide underwent a symmetry breaking crystallization process.
authors.affiliation: †Department of Chemistry, Konan University, 8-9-1 Okamoto, Higashinada-ku, Kobe 658-8501, Japan.
authors.forename: Kosuke
authors.initials: K
authors.lastname: Katagiri
authors.affiliation: ‡Kagawa School of Pharmaceutical Sciences, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan.
authors.forename: Shinsuke
authors.initials: S
authors.lastname: Komagawa
authors.affiliation: §Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.|∥Advanced Elements Chemistry Research Team, RIKEN Center for Sustainable Resource Science, and Elements Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan.
authors.forename: Masanobu
authors.initials: M
authors.lastname: Uchiyama
authors.affiliation: ‡Kagawa School of Pharmaceutical Sciences, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan.
authors.forename: Kentaro
authors.initials: K
authors.lastname: Yamaguchi
authors.affiliation: ⊥Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan.
authors.forename: Isao
authors.initials: I
authors.lastname: Azumaya