A Diastereoselective Route to Benzoannelated Bridged Sultams

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