Synthesis of 3-aryl-4-methyl-1,2-benzenedisulfonimides, new chiral Brønsted acids. A combined experimental and theoretical study |
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Authors: | Margherita BarberoStefano Bazzi Silvano CadamuroLorenzo Di Bari Stefano Dughera Giovanni Ghigo Daniele PadulaSilvia Tabasso |
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Institution: | a Dipartimento di Chimica Generale e Chimica Organica, Università di Torino, C.so Massimo d’Azeglio 48, 10125 Torino, Italy b Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Risorgimento 35, 56126 Pisa, Italy |
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Abstract: | We have recently reported the use, in catalytic amounts, of 1,2-benzenedisulfonimide as a safe Brønsted acid in some acid-catalyzed organic reactions. With the design of new and chiral acid organocatalysts with the structure of 1,2-benzenedisulfonimide in mind, we herein propose a synthesis of 1,2-benzenedisulfonimide derivatives bearing an aryl group in the 3-position with good overall yields. The chirality of these compounds is due to the hindered rotation of the aryl group (atropisomerism). We resolved the atropisomers of one of these compounds. |
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Keywords: | Atropisomerism Brø nsted acids Density functional calculations 3-Arylanthranilic acids Sulfonimides |
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