Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 12, Pages 2012-2016Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201501139
Keywords
amines; reactive intermediates; rearrangement; sulfamides; synthetic methods
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Funding
- Fondation de Cooperation Scientifique Campus Paris Saclay
- French National Research Agency [ANR-10-IDEX-0003-02]
- CNRS
- Universite de Versailles-St-Quentin-en-Yvelines
- Agence Nationale de la Recherche (ANR) [ANR-10-IDEX-0003] Funding Source: Agence Nationale de la Recherche (ANR)
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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.
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