Gold(<scp>I</scp>)‐Catalyzed Cyclizations of 1,6‐Enynes: Alkoxycyclizations and <i>exo</i>/<i>endo</i> Skeletal Rearrangements

Nieto‐Oberhuber, Cristina; Muñoz, María Paz; López, Susana Torío; Jiménez‐Núñez, Eloísa; Nevado, Cristina; Herrero‐Gómez, Elena; Raducan, Mihai; Echavarren, Antonio M.

doi:10.1002/chem.200501088

Cited by 372 publications

(261 citation statements)

References 102 publications

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“…[11,28] The minor product 162 corresponded to the expected cycloisomerization process, which was discussed above. The major product, however, was determined to be methylenecyclohexene 161, corresponding to a new reaction manifold.…”

Section: Conversion Of 16-enynes To Methylenecyclohexenesmentioning

confidence: 96%

“…In 2004, as a part of their comprehensive study of gold-based catalysis of enyne cycloisomerizations, Echavarren and co-workers reported that cationic gold complexes were exceedingly effective in promoting alkoxycarbocyclizations of a wide range of 1,6-enynes. [11,28] A representative scope of this process, as well as the typical reaction conditions, is shown in Scheme 27.…”

Section: Formation Of Alkyl-and Alkenylmethylenecyclopentanes and Cycmentioning

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: Conversion Of 16-enynes To Methylenecyclohexenesmentioning

confidence: 96%

Section: Formation Of Alkyl-and Alkenylmethylenecyclopentanes and Cycmentioning

confidence: 99%

Gold and Platinum Catalysis of Enyne Cycloisomerization

2006

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“…[168] Malacria et al [132] hatten schon früher die Reaktivität von Eninamiden in Gegenwart von Platin untersucht und eine ähnliche Reaktivität festgestellt, wenn auch bei höherer Temperatur [siehe Gl. [149,150,173] oder auf Gold(III)-Vorstufen [115,174] [Gl. (152) + zu erzeugen.…”

Section: Enin-tandemreaktionenunclassified

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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“…[8] The similarity be- tween KITPHOS and Buchwalds biaryl monophosphines, combined with the fact that the latter have proven to be very successful ligands for a vast array of gold-catalysed transformations [9] prompted us to synthesise gold complexes of these KITPHOS monophosphines and investigate their applications in a selection of gold-catalysed cycloisomerisations.…”

mentioning

confidence: 99%