The construction of stereochemically-rich 10-membered benzofused sultams via a one-pot, sequential protocol entailing an aziridine ring opening and intramolecular nucleophilic aromatic substitution (SNAr) is reported. The highly efficient method for the synthesis of benzo-fused sulfonyl-linked aziridines from amino alcohols is discussed. Microwave-assisted, one-pot aziridine ring opening with a hydroxyl-functionalized amine allows for robust intramolecular SNAr cyclization to furnish 10-membered sultam analogs. This approach employs a variety of amino alcohols as chiral building blocks for the preparation of medium-sized polycyclic sultam libraries that will be submitted for biological screening.

One-pot, sequential ring opening and SNAr: From aziridine to 10- and 11-membered benzo-fused sultams

251st National Meeting (2016)

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