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

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. © 2011 Elsevier Ltd. All rights reserved.