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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

chiral-disulfonimides

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

chiral-disulfonimides-catalyst

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

chiral-disulfonimides-collaboration

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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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