A facile method for intermolecular olefin aziridination is reported wherein sulfamate esters are used as the nitrogen source. Our general approach consists of first introducing a sulfamate group to a free alcohol of per-O-protected sugar derivatives. This forms carbohydrate cores along with one hydroxyl group derivatized as a sulfamate (sugar-OSO<sub>2</sub>NH<sub>2</sub>) which are known to be potential drug candidates. Secondly, these carbohydrate-based sulfamate esters are reacted with a structurally and electronically diverse range of olefins in the presence of various rhodium sources and oxidants. This represents one of the first methodologies that permits conjugating a carbohydrate molecule with a non-carbohydrate molecule under rhodium-catalysis in an intermolecular fashion.

Intermolecular aziridination using carbohydrate-derived sulfamates

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ACS Fall 2022

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