Abstract

AbstractAlthough nucleophilic aromatic substitution (SNAr) and many nucleophilic epoxide ring‐opening reactions proceed under similar anionic conditions, the literature examples of using these reactions in tandem for the construction of heterocyclic compounds are scarce. In this article, we disclose a detailed account of the synthesis of benzothiaoxazepine‐1,1‐dioxide‐containing fused‐ and linked‐biheterocycles by a base‐mediated, exo‐selective intramolecular epoxide‐opening/intramolecular nucleophilic aromatic substitution cascade of epoxide‐tethered ortho‐fluorobenzenesulfonamides. A wide range of substrates exhibited high overall yields and complete regio‐ and diastereoselectivity

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