Stereoselective Synthesis of Isoxazolinobenzoxepanes via Intramolecular Nitrile Oxide Cycloaddition

Abstract

Concise routes to the synthesis of indole-tethered nitrile oxides have been developed, and their intramolecular nitrile oxide cycloadditions were studied. Heterocyclic scaffolds involving isoxazolinobenzoxepane frameworks have been achieved via intramolecular nitrile oxide cycloaddition of 3-[1-(2-allyloxyphenyl)-2-nitroethyl]-1H-indole derivatives using (Boc)₂O and DMAP. This protocol affords products with excellent trans-selectivity.

intramolecular nitrile oxide cycloaddition - Michael addition - isoxazolinobenzoxepanes - trans-selectivity

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Crystallographic data of compound 7e reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplemental publication No. CCDC-775950. Copies of the data can be obtained, free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: [phone] or email: [e-mail]].