Spontaneous Resolution of Aromatic Sulfonamides: Effective Screening Method and Discrimination of Absolute Structure

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• 作者：Takako Kato ; Iwao Okamoto ; Aya Tanatani ; Terutaka Hatano ; Masanobu Uchiyama ; Hiroyuki Kagechika ; Hyuma Masu ; Kosuke Katagiri ; Masahide Tominaga ; Kentaro Yamaguchi ; Isao Azumaya
• 刊名：Organic Letters
• 出版年：2006
• 出版时间：October 26, 2006
• 年：2006
• 卷：8
• 期：22
• 页码：5017 - 5020
• 全文大小：866K
• 年卷期：v.8,no.22(October 26, 2006)
• ISSN：1523-7052

文摘

An effective screening method combining parallel synthesis and solid-state CD measurements was established to identify achiral aromaticsulfonamides that show spontaneous resolution with rapidity. We found that 4 of the 12 achiral sulfonamides crystallized as chiral crystalsthrough 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.