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Synthesis of N‑Acyl Sulfamates from Fluorosulfates and Amides

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journal contribution
posted on 2018-12-24, 00:00 authored by Philippe Gilles, Cedrick Veryser, Sarah Vangrunderbeeck, Sam Ceusters, Luc Van Meervelt, Wim M. De Borggraeve
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.

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