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

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

References

1. Mahlau M, List B. 2013. Asymmetric Counteranion-Directed Catalysis: Concept, Definition, and Applications. Angew. Chem. Int. Ed.. 52(2):518-533. https://doi.org/10.1002/anie.201205343

2. Mayer S, List B. 2006. Asymmetric Counteranion-Directed Catalysis. Angew. Chem. Int. Ed.. 45(25):4193-4195. https://doi.org/10.1002/anie.200600512

3. García-García P, Lay F, García-García P, Rabalakos C, List B. 2009. A Powerful Chiral Counteranion Motif for Asymmetric Catalysis. Angew. Chem. Int. Ed.. 48(24):4363-4366. https://doi.org/10.1002/anie.200901768

4. Ratjen L, García-García P, Lay F, Beck ME, List B. 2011. Disulfonimide-Catalyzed Asymmetric Vinylogous and Bisvinylogous Mukaiyama Aldol Reactions. Angew. Chem. Int. Ed.. 50(3):754-758. https://doi.org/10.1002/anie.201005954

5. Chen L, He H, Chan W, Lee AWM. 2011. Chiral Sulfonimide as a Brønsted Acid Organocatalyst for Asymmetric Friedel?Crafts Alkylation of Indoles with Imines. J. Org. Chem.. 76(17):7141-7147. https://doi.org/10.1021/jo2011335

6. Gandhi S, List B. 2013. Catalytic Asymmetric Three-Component Synthesis of Homoallylic Amines. Angew. Chem. Int. Ed.. 52(9):2573-2576. https://doi.org/10.1002/anie.201209776