Intramolecular cyclization of 1-nitroalkenyl radicals generated by one-electron oxidation of aci-nitro anions with CAN: stereoselective formation of 3,4-functionalized tetrahydrofurans

Abstract

Upon one-electron oxidation by ammonium hexanitratocerate(IV) (CAN), aci-nitro anions 3a-d resulting from oxa-Michael addition of allylic alcohol to α,β-disubstituted nitroalkenes 1a-d undergo stereoselective radical cyclization into 3-nitro-4-nitrooxymethyltetrahydrofurans 6a-d and 3-nitro-4-hydroxymethyltetrahydrofurans 7,8a-d.