Photoinduced radical reactions of α-alkylated ethyl 2-oxo-1-cyclopentanecarboxylate derivatives: α-cleavage and cyclization to the skeleton of linear cyclohexano …

NT Tzvetkov, PA Waske, B Neumann, HG Stammler…

Index: Tzvetkov, Nikolay T.; Waske, Prashant A.; Neumann, Beate; Stammler, Hans-Georg; Mattay, Jochen Tetrahedron Letters, 2008 , vol. 49, # 10 p. 1710 - 1713

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Abstract

The tricyclic core of linear cyclohexano diquinanes was synthesized using photoinduced electron transfer (PET) as a key step. The reaction proceeded in high regioselective manner via ketyl radical anions leading to distonic δ-keto radical anion as reactive intermediates. The irradiation was carried out at a wavelength of 254nm with triethylamine (TEA) as a strong reducing reagent in acetonitrile. We also showed that the photolysis of the α- ...