Efficient Synthesis of Unsymmetrical Sulfamides via a Lossen-Like Rearrangement

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• 作者：Loï ; c Pantaine ; Franç ; ois Richard ; Jé ; rô ; me Marrot ; Xavier Moreau ; Vincent Coeffard and Christine Greck
• 刊名：Advanced Synthesis & Catalysis
• 出版年：2016
• 出版时间：June 16, 2016
• 年：2016
• 卷：358
• 期：12
• 页码：2012-2016
• 全文大小：507K
• ISSN：1615-4169

文摘

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.