title: Spontaneous resolution of aromatic sulfonamides: effective screening method and discrimination of absolute structure.
abstract: An effective screening method combining parallel synthesis and solid-state CD measurements was established to identify achiral aromatic sulfonamides that show spontaneous resolution with rapidity. We found that 4 of the 12 achiral sulfonamides crystallized as chiral crystals through this method. The chirality of each sulfonamide was discriminated by solid-state CD spectra and Flack parameter in an X-ray analysis. Correspondence between the observed Cotton effect and the absolute configuration could be confirmed by time-dependent DFT calculations. [structure: see text]
authors.affiliation: Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan.
authors.forename: Takako
authors.initials: T
authors.lastname: Kato
authors.forename: Iwao
authors.initials: I
authors.lastname: Okamoto
authors.forename: Aya
authors.initials: A
authors.lastname: Tanatani
authors.forename: Terutaka
authors.initials: T
authors.lastname: Hatano
authors.forename: Masanobu
authors.initials: M
authors.lastname: Uchiyama
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Kagechika
authors.forename: Hyuma
authors.initials: H
authors.lastname: Masu
authors.forename: Kosuke
authors.initials: K
authors.lastname: Katagiri
authors.forename: Masahide
authors.initials: M
authors.lastname: Tominaga
authors.forename: Kentaro
authors.initials: K
authors.lastname: Yamaguchi
authors.forename: Isao
authors.initials: I
authors.lastname: Azumaya
mesh_terms: D002625:Chemistry, Organic / Q000379:methods*; D002942:Circular Dichroism; D015394:Molecular Structure; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D013449:Sulfonamides