pH-Controlled Chirality Inversion in Enantiodifferentiating Photocyclodimerization of 2-Antharacenecarboxylic Acid Mediated by Î³-Cyclodextrin Derivatives.

Kanagaraj, Kuppusamy; Liang, Wenting; Rao, Ming; Yao, Jiabin; Wu, Wanhua; Cheng, Guo; Ji, Jiecheng; Wei, Xueqin; Peng, Chao; Yang, Cheng

Kanagaraj, Kuppusamy; Liang, Wenting; Rao, Ming; Yao, Jiabin; Wu, Wanhua; Cheng, Guo; Ji, Jiecheng; Wei, Xueqin; Peng, Chao; Yang, Cheng.

Afiliação

Kanagaraj K; Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China.
Liang W; Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China.
Rao M; Institute of Environmental Science, Shanxi University, Taiyuan 030006, China.
Yao J; Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China.
Wu W; Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China.
Cheng G; Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China.
Ji J; Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China.
Wei X; Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China.
Peng C; School of Pharmacy, Guangxi Medical University, Nanning 530021, China.
Yang C; Key Laboratory of Green Chemistry & Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, Chengdu 610064, China.

Org Lett ; 22(14): 5273-5278, 2020 07 17.

Article em En | MEDLINE | ID: mdl-32418431

ABSTRACT

ABSTRACT

Several Î³-cyclodextrin (Î³-CDx) derivatives were used as chiral hosts for the photocyclodimerization of 2-anthracenecarboxylic acid (AC). The effect of pH on photoreactivity and stereochemical outcome of photoproducts was investigated. Upon changing the solution pH, the stereochemical outcome of HH cyclodimer 3 was inverted from 25.2% to -64.4% and 41.2% to -76.2%, respectively, in the photocyclodimerization of AC mediated by bis-quinoline-modified Î³-CDx 7 and its N-methylated derivative 8.

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2020 Tipo de documento: Article País de afiliação: China

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