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Synlett 2000; 2000(5): 0731-0733
DOI: 10.1055/s-2000-6608
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Intramolecular 6-exo Cyclization of 1-Nitro-6-heptenyl Radicals Generated by One-Electron Oxidation of Aci-Nitroanions with CAN: A Completely Stereoselective Formation of 2,3,4-Trisubstituted Tetrahydropyrans

Anne-Catherine Durand* , Jean Rodriguez, Jean-Pierre Dulcère
  • *RéSo, Réactivité en Synthèse Organique, UMR 6516, Faculté des Sciences et Techniques de St Jérôme, Boîte D 12, Av. Esc. Normandie-Niemen, 13397, Marseille Cedex 20, France; Fax + 33(4)91 28 88 41; E-mail: jean-pierre.dulcere@reso.u-3mrs.fr
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Publication Date:
31 December 2000 (online)

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Upon one-electron oxidation by ammonium hexanitratocerate (IV) (CAN), aci-nitroanions 3a - d resulting from oxa-Michael addition of homoallylic alcohol to α,β-disubstituted nitroalkenes 1a - d undergo radical cyclization to afford stereoselectively 2,3-dialkyl-4-methyl tetrahydropyrans 6a - d.

α-nitro-alkenyl radicals - stereoselective radical cyclization - 2,3,4-trisubstituted tetrahydropyrans - CAN