A Diastereoselective Route to Benzoannelated Bridged Sultams

Abstract A practical diastereoselective method for the synthesis of benzoannelated tri- and tetracyclic bridged sultams has been developed. The synthetic route employs widely available, substituted o -iodoanilines and is based on intramolecular Michael addition followed by cycloalkylation with α,ω-dihaloalkanes, or vice versa. The target compounds were isolated in good yields and the diastereoselectivity of the reaction could be easily controlled by the order of Michael addition and cycloalkylation steps.