4 years ago

Gold(I)-Catalyzed Cycloisomerization–Dimerization Cascade of Benzene-Tethered 1,6-Enynes

Gold(I)-Catalyzed Cycloisomerization–Dimerization Cascade of Benzene-Tethered 1,6-Enynes
María C. de la Torre, María Frutos, Catherine Hemmert, Heinz Gornitzka, Alma Viso, Mónica Álvarez-Pérez, Roberto Fernández de la Pradilla, Miguel A. Sierra
An unprecedented stereoselective domino reaction of 1,6-enynes with an aryl ring at C3–C4 in the presence of gold(I) catalysts at low temperature is described. This process involves a novel 5-exo-dig cycloisomerization–dimerization sequence to afford formal Diels–Alder adducts that undergo a smooth gold-catalyzed double bond migration at room temperature. In addition, the first examples of the gold mesoionic carbene mediated [2+2+2] cycloaddition of these enynes with benzaldehyde are reported.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01273

DOI: 10.1021/acs.joc.7b01273

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