ol5b01455_si_001.cif (169.36 kB)
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
dataset
posted on 2015-08-07, 00:00 authored by Kosuke Katagiri, Shinsuke Komagawa, Masanobu Uchiyama, Kentaro Yamaguchi, Isao AzumayaA 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.