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Kaufman, Riley H; Law, Chunyin M; Simanis, Justin A; Woodall, Erica L; Zwick, Christian R; Wedler, Henry B; Wendelboe, Paul; Hamaker, Christopher G; Goodell, John R; Tantillo, Dean J; Mitchell, T. Andrew
Journal of organic chemistry, 09/2018, Letnik: 83, Številka: 17Journal Article
Oxidopyrylium-alkene 5 + 2 cycloaddition conjugate addition cascade (C3) sequences are described. Intramolecular cycloadditions involving terminal alkenes, enals, and enones were investigated. Substrates with tethers of varying lengths delivered five- and six-membered carbocycles and heterocycles thus demonstrating the scope and limitation of the cycloaddition–conjugate addition cascade. Several experiments and theoretical calculations provide evidence for the proposed mechanistic pathway.
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