Chiral Disulfonimides for Asymmetric Counteranion-directed Catalysis (ACDC)

Introduction

Asymmetric counteranion-directed catalysis (ACDC) has 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.

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

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