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Efficient Synthesis of Unsymmetrical Sulfamides via a Lossen‐Like Rearrangement
Author(s) -
Pantaine Loïc,
Richard François,
Marrot Jérôme,
Moreau Xavier,
Coeffard Vincent,
Greck Christine
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201501139
Subject(s) - chemistry , inert gas , combinatorial chemistry , solvent , organic chemistry
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.