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

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

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...

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Veröffentlicht in:Journal of organic chemistry 2017-07, Vol.82 (14), p.7546-7554
Hauptverfasser: Álvarez-Pérez, Mónica, Frutos, María, Viso, Alma, Fernández de la Pradilla, Roberto, de la Torre, María C, Sierra, Miguel A, Gornitzka, Heinz, Hemmert, Catherine
Format: Artikel
Sprache:eng
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Chemical Sciences
Coordination chemistry
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b01273