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Chiral Disulfonimides: New Products for Asymmetric Counteranion Directed Catalysis (ACDC)

Introduction

In recent years, asymmetric counteranion-directed catalysis (ACDC) has found a number of valuable applications in enantioselective synthesis.1 Beginning in 2006, Benjamin List2 and others have expanded this field to encompass a broad range of useful transformations.

Sigma-Aldrich is proud to offer the newest class of catalyst used in this highly promising activation mode, available in both enantiomeric forms.

Representative Applications

In 2009, List and coworkers reported that disulfonimide catalyst 790753 can be used to catalyze asymmetric Mukaiyama aldol reactions in up to 94% ee.3 Two years later, this reaction was extended to vinylogous and bisvinylogous reactions as well.4

 

More recently, 790753 was employed as a Brønsted acid catalyst in the asymmetric Friedel-Crafts alkylation of imines with indoles.5

 

Finally, disulfonamide catalyst 790842 was successfully employed in the three-component synthesis of homoallylic amines in up to 97% ee.6


To learn more about other products in our catalog that have been established in collaboration Prof. Dr. List, please visit his Professor Product Page.

Materials

     
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