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.

Synthesis of 3-aryl-4-methyl-1,2-benzenedisulfonimides, new chiral Brønsted acids. A combined experimental and theoretical study

BARBERO, Margherita;CADAMURO, Silvano;DUGHERA, Stefano;GHIGO, Giovanni;TABASSO, Silvia
2011-01-01

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.
67
5789
5797
http://www.sciencedirect.com/science/article/pii/S0040402011008386
Atropisomerism; Brønsted acids; Density functional calculations; 3-Arylanthranilic acids; Sulfonimides
Margherita Barbero; Stefano Bazzi; Silvano Cadamuro; Lorenzo Di Bari; Stefano Dughera; Giovanni Ghigo; Daniele Padula; Silvia Tabasso
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/88216
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