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Gold(I)‐katalysierte Diastereoselektive Hydroacylierung Terminaler Alkine Mit Glyoxalen

Shuai Shi, T. Wang, Vanessa Weingand, M. Rudolph, A. Hashmi, A. Hashmi
Published 2014 · Chemistry

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Die Reaktion eines α-Ketoaldehyds und eines terminalen Alkins in Gegenwart von Piperidin und einer katalytischen Menge von AuCl liefert 1,2-Dicarbonyl-3-ene, Produkte einer formalen Hydroacylierung der Dreifachbindung. Die Anwendungsbreite der Methode ist gros, verschiedene Arylsubstituenten an der Dicarbonyleinheit oder dem Alkin werden gut toleriert. Die Produkte konnen selektiv in Vinylchinoxaline uberfuhrt werden. Mechanistische Studien, inklusive Isotopenmarkierungsexperimente, weisen darauf hin, dass zunachst eine A3-Umsetzung zu Propargylaminen fuhrt und eine darauffolgende basenvermittelte Alkin/Allen-Umlagerung und eine Hydrolyse der Enaminteilstruktur wahrend der Aufarbeitung das formale Hydroacylierungsprodukt liefern.
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