Issue 38, 2020

Five-membered cyclic sulfamidate imines: versatile scaffolds for organic synthesis

Abstract

In recent years, five-membered ring cyclic sulfamidate imines (5H-1,2,3-oxathiazole 2,2-dioxides) have received increasing attention as useful precursors for the stereoselective synthesis of many valuable heterocycles. Bearing a reactive N-sulfonyl imine moiety as part of the stereodefined skeleton, this sulfamidate imine platform has been utilised as a substrate in many reactions, including nucleophilic additions and reductions, to prepare highly functionalised cyclic sulfamidates. In addition, cyclic sulfamidate imines can also readily participate as nucleophiles in many chemical transformations, owing to the acidic proton(s) adjacent to the imine moiety. This short review highlights recent developments involving cyclic sulfamidate imines, including their synthesis and reactivity, with a focus on stereoselective processes.

Graphical abstract: Five-membered cyclic sulfamidate imines: versatile scaffolds for organic synthesis

Article information

Article type
Review Article
Submitted
30 Jul 2020
Accepted
08 Sep 2020
First published
08 Sep 2020

Org. Biomol. Chem., 2020,18, 7467-7484

Five-membered cyclic sulfamidate imines: versatile scaffolds for organic synthesis

Q. H. Pham, C. J. T. Hyland and S. G. Pyne, Org. Biomol. Chem., 2020, 18, 7467 DOI: 10.1039/D0OB01568G

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