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Li, Lei; Turnbull, William L.; McDonald, Robert; West, F. G.
European journal of organic chemistry, April 26, 2021, Letnik: 2021, Številka: 16Journal Article
3‐Acyl‐4‐hydroxypyan‐2‐ones with pendent furans, readily available from dehydroacetic acid, are substrates for intramolecular 4+4‐photocycloaddition. In the presence of stoichiometric lithium base, these substrates undergo conversion to lactone‐bridged cyclooctenones in moderate to good yields upon irradiation in THF at 0 °C. In contrast to other crossed 4+4‐photocycloadditions of pyran‐2‐ones, these examples proceed with complete diastereoselectivity for the endo cycloadducts. Readily accessible 3‐acyl‐4‐hydroxypyran‐2‐ones with pendent furans undergo 4+4‐photocycloaddition reactions in the presence of lithium ion to afford lactone‐bridged cyclooctenones with complete selectivity for the endo cycloadducts.
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