Spontaneous resolution of aromatic sulfonamides: effective screening method and discrimination of absolute structure |
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Authors: | Kato Takako Okamoto Iwao Tanatani Aya Hatano Terutaka Uchiyama Masanobu Kagechika Hiroyuki Masu Hyuma Katagiri Kosuke Tominaga Masahide Yamaguchi Kentaro Azumaya Isao |
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Affiliation: | Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan. |
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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] |
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