Regioselective synthesis of aza-saccharins <i>via</i> anionic [1,4] Fries-type rearrangement of aryl sulfonimidoyl fluorides

2026/01/01 by Mario Leypold, Lorenzo Poli, Max Earl +18 · 1 voice
Chemistry · Pharmacology, Toxicology and Pharmaceutics · #Synthesis and Catalytic Reactions #Fluorine in Organic Chemistry #Sulfur-Based Synthesis Techniques

paper · pdf · doi:10.1039/d6sc00432f

openalex publication_date 2026/01/01 · openalex created_date 2026/04/30 · openalex updated_date 2026/06/14

Abstract

SuFEx capture proceeds stereospecifically with inversion at sulfur. This synthetic method provides a mechanistically defined and stereocontrolled entry to chiral aza-saccharins with potential relevance to medicinal chemistry, agrochemical discovery and related disciplines.

Citations

• Synthesis of Six-Membered Cyclic Sulfonimidamides
• The stereochemistry of substitution at S( <scp>vi</scp> )

Discussions

• A short synthesis of aza-saccharins through anionic Fries Rearrangement. A fun project, thanks Mario Leypold and Karolina Kwapien for bringing me into this! doi.org/10.1039/d6sc... [bsky, 0 points, 0 comments]

Related

• Regiospecific anomerisation of acylated glycosyl azides and benzoylated disaccharides by using TiCl4.
• Stereocontrolled Syntheses of Seven‐Membered Carbocycles by Tandem Allene Aziridination/[4+3] Reaction
• Tunable thiofumarate stereoselective cycloadditions <i>via</i> aminomefloquine catalysis
• Specificity and Stereoselectivity of Cryptic Sulfotransferases
• Stereoselective Synthesis of α‐Azido Esters and α‐Amino Acid Derivatives via Matteson Homologation of Boronic Esters