Upcoming Chemistry Cells, Biochemistry & Physiology

New groups for energy transfer catalysis and the synthesis of sulfur heterocycles

Summary

Original abstract (not yet simplified)

Sulfonamides are present multiple FDA approved medicines, and their mono-aza variants, sulfonimidamides, are now also appearing regularly in the medicinal chemistry patent literature. However, the cyclic variants of these molecules are only sparsely present in the chemical literature, despite isolated examples demonstrating encouraging bio-activity. A significant contributor to this absence is the lack of appealing synthetic methods. In this proposal...

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Sulfonamides are present multiple FDA approved medicines, and their mono-aza variants, sulfonimidamides, are now also appearing regularly in the medicinal chemistry patent literature. However, the cyclic variants of these molecules are only sparsely present in the chemical literature, despite isolated examples demonstrating encouraging bio-activity. A significant contributor to this absence is the lack of appealing synthetic methods. In this proposal we show how photocatalyzed cycloadditions between sulfinylamine reagents and varied unsaturated coupling partners can be used to access functionalised cyclic variants of sulfonamides and sulfonimidamides. The reactions will be promoted using Energy Transfer (EnT) catalysis. Extensions of the chemistry to access the corresponding di-aza variants, sulfondiimidamides, and to the control of stereochemistry at the sulfur centre, will also be explored.

Related Research

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Rapid access to diverse and stereochemically enriched cyclic aza-sulfur(VI) compounds
Late-stage sulfonamidation, and sulfonimidamidation for drug discovery
New sulfur-based reactive intermediates for synthesis and catalysis
Stereoselective Synthesis of aza-Sulfur(VI) Motifs as Design Elements for Drug Discovery
Integrating sulfonium salt photochemistry with biocatalytic imine reduction: enantioselective synthesis of phenylethylamines

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