PtCl<sub>2</sub>-Catalyzed Cycloisomerizations of 5-En-1-yn-3-ol Systems

Harrak, Youssef; Blaszykowski, Christophe; Bernard, Matthieu; Cariou, Kevin; Mainetti, Emily; Mouriès, Virginie; Dhimane, Anne‐Lise; Fensterbank, Louis; Malacrìa, Max

doi:10.1021/ja0474695

Cited by 234 publications

(82 citation statements)

References 13 publications

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“…[36] The deuterium label in the product appeared exclusively at the C (2) The studies of Malacria and co-workers are summarized in Scheme 46 and Scheme 47. [37] This work demonstrated that enynes containing terminal alkynes successfully participated in the cycloisomerization process. In addition, the authors established that the formation of bicycloA C H T U N G T R E N N U N G [3.1.0]hexenes was stereospecific.…”

Section: Formation Of Bicycloa C H T U N G T R E N N U N G [310]alkmentioning

confidence: 81%

“…[36,37] These reports were soon followed by a communication from the Toste laboratory, describing a series of independently observed cycloiso- merizations of 1,5-enynes, which were catalyzed by cationic gold-phosphine complexes. [38] Fürstner and co-workers reported that subjection of enyne 200 to a catalytic amount of PtCl 2 in toluene at 60 8C afforded bicyclic ketone 201 in 75 % yield (Scheme 44).…”

Section: Formation Of Bicycloa C H T U N G T R E N N U N G [310]alkmentioning

confidence: 99%

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Gold and Platinum Catalysis of Enyne Cycloisomerization

2006

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This account provides a comprehensive overview of the development of gold and platinum catalysis of the enyne cycloisomerization. The use of these soft, alkynophilic metals enables mild, chemoselective and efficient transformations of a variety of readily available acyclic enynes to a wide range of synthetically useful carbocyclic and heterocyclic products. The review is organized according to diverse structural types of enynes that undergo skeletal cycloisomerizations. The account begins with an overview of transformations of primarily 1,6-enynesheptenes. This section is followed by the discussion of cycloisomerizations of 1,5-enynes, which enable a rapid access to a range of other cyclic products, including bicycloA C H T U N G T R E N N U N G [3.1.0]hexenes, cyclohexadienes, heterobicycloalkenes, methylenecyclopentenes, naphthalenes and methyleneindenes. In addition, the [3,3] rearrangement of 1,5-enynes provides efficient access to the corresponding allenes. The account concludes with an overview of the most recent studies on gold-and platinum-catalyzed cycloisomerizations of 1,4-and 1,3-enynes. Due to the rapidly increasing interest in this area during the past three to five years, we believe that this review provides a timely and comprehensive discussion of the development gold-and platinum-catalyzed cycloisomerization starting from the initial pioneering investigations to the latest advances in the field. A significant emphasis is placed on the mechanistic discussion of the observed manifolds of skeletal reorganizations.

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Section: Formation Of Bicycloa C H T U N G T R E N N U N G [310]alkmentioning

confidence: 81%

Section: Formation Of Bicycloa C H T U N G T R E N N U N G [310]alkmentioning

confidence: 99%

Gold and Platinum Catalysis of Enyne Cycloisomerization

2006

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“…Echavarren et al [128] untersuchten speziell Enolether als Alkenpartner in dieser Cycloisomerisierungsreaktion. Die Arbeitsgruppen von Fürstner [129] und Malacria [130] erweiterten die Methode elegant auf 3-hydroxylierte 1,5-Enine. Fürstner [135] beschrieben [Gl.…”

Section: Enin-umlagerungenunclassified

“…Aufgrund von Markierungsexperimenten mit Deuterium [41,138] und DFT-Rechnungen [115,138] Anknüpfend an die Untersuchung der intermolekularen Variante dieser Umwandlung durch Ohe, Uemura und Miki [141] veröffentlichten die Arbeitsgruppen von Fürstner [129] und Malacria [130,142] [130] Durch Erweiterung des Konzepts auf 1,4-Enine haben Sarpong et al [143] …”

Section: Enin-umlagerungenunclassified

Cycloisomerisierungen von 1,n‐Eninen: faszinierende metallkatalysierte Umlagerungen und mechanistische Einblicke

2008

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Metallkatalysierte Cycloisomerisierungen von 1,n‐Eninen haben sich als konzeptionell und chemisch höchst attraktive Reaktionen erwiesen, da sie dem häufig geforderten Streben nach Atomökonomie nachkommen und neuartige Reaktionsverläufe ermöglichen. Seit den bahnbrechenden Arbeiten in der Gruppe von Barry Trost mit Palladium Mitte der 1980er Jahre wurden viele weitere Metalle als hervorragende Katalysatoren für Enin‐Gerüstumlagerungen identifiziert. Zudem kann das Verhalten von 1,n‐Eninen durch funktionelle Gruppen wie Alkohol‐, Aldehyd‐, Ether‐, Alken‐ oder Alkineinheiten beeinflusst werden, wodurch die Komplexität der synthetisierten Verbindungen zunimmt. Neben den eigentlichen 1,n‐Enin‐Umlagerungen wurden mehrere Tandemreaktionen entdeckt, die intramolekulare Abfangreagentien oder intermolekulare Partner einbeziehen. Diese Übersicht will die wichtigsten Beiträge auf diesem Gebiet der Katalyse behandeln und die mechanistischen Erkenntnisse zu den neuesten Entdeckungen darlegen und kommentieren.

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“…214 Thus, for example, the gold-catalyzed cyclization of the propargylic acetate in equation (74) gives the product of cyclization and 1,2-acetate migration, which was methanolyzed to yield the corresponding ketone. The first mechanistic pathway in equation (73) is probably followed when n = 2, as shown in a key Pt(II)-catalyzed cyclization for the synthesis of (−)-α-cubene and (−)-cubebol.…”

Section: 218mentioning

confidence: 99%