Efficient Synthesis of Unsymmetrical Sulfamides via a Lossen‐Like Rearrangement. Issue 12 (24th May 2016)

• Record Type: Journal Article
• Authors: Pantaine, Loïc; Richard, François; Marrot, Jérôme; Moreau, Xavier; Coeffard, Vincent; Greck, Christine
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 12(2016)
• Page Start: 2012
• Page End: 2016
• Publication Date: 2016-05-24
• Subjects: amines -- reactive intermediates -- rearrangement -- sulfamides -- synthetic methods; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201501139
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A convenient one‐pot synthesis of unsymmetrical sulfamides via a Lossen‐like rearrangement is reported. The protocol operates under simple conditions at room temperature and does not require an inert atmosphere and a dry solvent. The ability of N‐ hydroxy arenesulfonamide O ‐derivatives to generate under mild conditions N ‐sulfonylimine intermediates was a trigger point for developing a general synthetic strategy towards unsymmetrical sulfamides. The synthetic potential of the methodology has been investigated by preparing cyclic sulfamides and new potential chiral organocatalysts. Abstract :