Spontaneous resolution of aromatic sulfonamides: effective screening method and discrimination of absolute structure.
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]
Kato
Takako
T
Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan.
Okamoto
Iwao
I
Tanatani
Aya
A
Hatano
Terutaka
T
Uchiyama
Masanobu
M
Kagechika
Hiroyuki
H
Masu
Hyuma
H
Katagiri
Kosuke
K
Tominaga
Masahide
M
Yamaguchi
Kentaro
K
Azumaya
Isao
I
D002625:Chemistry, Organic / Q000379:methods*; D002942:Circular Dichroism; D015394:Molecular Structure; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry*
D013449:Sulfonamides