Intramolecular cyclization of 1-nitroalkenyl radicals generated by one-electron oxidation of aci-nitro anions with CAN: stereoselective formation of 3,4-functionalized tetrahydrofurans
- 1 January 1999
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 23,p. 2437-2438
- https://doi.org/10.1039/a907842h
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.Keywords
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