Issue 38, 2020

Chiral disulfonimides: a versatile template for asymmetric catalysis

Abstract

Since the emergence of pseudo-C2-symmetric chiral phosphoric acids (CPA), much work has been done to utilize these systems in stereoselective, organocatalytic processes. Despite the success in this field, reasonably basic substrates such as imines are often required to achieve appreciable activation. In order to access a wider variety of potential reaction partners, many related organocatalysts with enhanced Brønsted acidity have since been developed. Chiral disulfonimides (DSIs) have materialized as one such powerful class of organocatalysts and have been shown to expand the list of potential substrates to include aldehydes and ketones via Brønsted, Lewis, or bifunctional acid activation. This versatility renders DSIs amenable to an impressive scope of reaction types, typically with remarkable stereoselectivity induced by asymmetric counteranion-directed catalysis (ACDC). This review serves to provide a complete analysis of the successful applications, mechanistic insights, and unmet challenges exhibited to date in DSI-catalyzed and -assisted processes.

Graphical abstract: Chiral disulfonimides: a versatile template for asymmetric catalysis

Article information

Article type
Review Article
Submitted
23 8 2020
Accepted
25 8 2020
First published
31 8 2020

Org. Biomol. Chem., 2020,18, 7485-7513

Chiral disulfonimides: a versatile template for asymmetric catalysis

M. C. Benda and S. France, Org. Biomol. Chem., 2020, 18, 7485 DOI: 10.1039/D0OB01742F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements