Synthesis and chiroptical properties of cylindrical macrocycles comprising two calix[3]aramide moieties
Yuuki Saito1, Misa Satake, Ryuichi Mori
1Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan. isao.azumaya@phar.toho-u.ac.jp.
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.
More Related Videos
Related Concept Videos
Stereoisomerism of Cyclic Compounds
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Aromatic Hydrocarbon Anions: Structural Overview
Due to the absence of continuous...
Prochirality
Frost Circles for Different Conjugated Systems
Stability of Substituted Cyclohexanes
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...


