Synthesis of N-Acyl Sulfamates from Fluorosulfates and Amides

A novel synthetic strategy toward N-acyl sulfamates was developed. Interestingly, fluorosulfates, a new emerging class of electrophiles, were used to construct the sulfamate core. This precludes handling of chlorosulfonyl isocyanate and sulfamoyl chloride. In combination with amides, a wide and dive...

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Veröffentlicht in:The Journal of Organic Chemistry 2019-01, Vol.84 (2), p.1070-1078
Hauptverfasser: Gilles, Philippe, Veryser, Cedrick, Vangrunderbeeck, Sarah, Ceusters, Sam, Van Meervelt, Luc, De Borggraeve, Wim M
Format: Artikel
Sprache:eng
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Zusammenfassung:A novel synthetic strategy toward N-acyl sulfamates was developed. Interestingly, fluorosulfates, a new emerging class of electrophiles, were used to construct the sulfamate core. This precludes handling of chlorosulfonyl isocyanate and sulfamoyl chloride. In combination with amides, a wide and diverse set of N-acyl sulfamates was synthesized, including functionalized bioactive compounds. Furthermore, initial results showed that this method is also amenable to access N-thioacyl sulfamates.
ISSN:0022-3263