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.

Key words

heterocycles - bridged sultams - Michael addition - cycloalkylation - diastereoselective synthesis

Publication History

Received: 12 May 2021

Accepted after revision: 17 June 2021

Accepted Manuscript online:
17 June 2021

Article published online:
04 August 2021

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