title: Diastereoselective cyclization of an aminobenzoic acid derivative and chiroptical properties of triple-stranded helical bis(phenylethynyl)benzene.
abstract: The diastereoselective cyclization of 2,5-dibromo-4-hexylaminobenzoic acid was achieved by the microwave-assisted condensation using SiCl4. Moreover, the triple-stranded helical structure of bis(phenylethynyl)benzene units embedded in the cyclic tri(benzamide) scaffold was obtained by a Sonogashira-Hagihara coupling reaction. Two optically active enantiomers that do not racemize even at the elevated temperature were separated by chiral HPLC. The chiral helical topology was revealed by the spectroscopic data and theoretical calculation.
authors.affiliation: Department of Materials Science and Engineering, Nagoya Institute of Technology, Gokiso, Showa, Nagoya, Aichi 466-8555, Japan. takagi.koji@nitech.ac.jp.
authors.forename: Ryohei
authors.initials: R
authors.lastname: Yamakado
authors.forename: Shin-ichi
authors.initials: S
authors.lastname: Matsuoka
authors.forename: Masato
authors.initials: M
authors.lastname: Suzuki
authors.forename: Daisuke
authors.initials: D
authors.lastname: Takeuchi
authors.forename: Hyuma
authors.initials: H
authors.lastname: Masu
authors.forename: Isao
authors.initials: I
authors.lastname: Azumaya
authors.forename: Koji
authors.initials: K
authors.lastname: Takagi
mesh_terms: D062365:Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D062365:Aminobenzoates; D001555:Benzene Derivatives