Novel 1,3-diene synthesis from alkyne and ethylene by ruthenium-catalyzed enyne metathesis

Kinoshita, Atsushi; Sakakibara, Norikazu; Mori, Miwako

doi:10.1016/s0040-4020(99)00297-5

Cited by 100 publications

(54 citation statements)

References 53 publications

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“…[39,40] In enyne metathesis, alkynes 17-19 underwent ethylene metathesis in poor yields, ostensibly due to chelation. [41] Chelation in the vinyl carbene complexes is thought to occur via structures such as 20-22. However, limited evidence for chelation means that there is limited structural information available in order to predict which motifs will lead to chelation.…”

Section: Tandem Metathesis-mentioning

confidence: 99%

Ruthenium vinyl carbene intermediates in enyne metathesis

Diver

2007

Coordination Chemistry Reviews

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This review provides an overview of ruthenium vinyl carbene reactivity as it relates to enyne metathesis. Methods for the synthesis of metathesis-active and metathesis-inactive complexes are also summarized. Some of the early hypotheses about vinyl carbene intermediates in enyne metatheses were tested in the arena of synthetic chemistry and subsequently led to mechanistic studies. In these two areas, studies from the author's labs are described. There are still many unresolved questions in enyne metathesis that trace back to vinyl carbene reactivity. Hopefully this review will stimulate further investigation into vinyl carbene reactivity which should further refine our understanding of catalytic enyne metathesis.

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Section: Tandem Metathesis-mentioning

confidence: 99%

Ruthenium vinyl carbene intermediates in enyne metathesis

Diver

2007

Coordination Chemistry Reviews

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“…[15] On the other hand, the cross-metathesis of an alkyne and ethylene was developed in 1997. [16] When a CH 2 Cl 2 solution of alkyne 8 was stirred under an atmosphere of ethylene at room temperature in the presence of 1c, 1,3-diene 9 was obtained. It is interesting that, formally, the double bond of ethylene is cleaved and each methylene part is introduced onto the alkyne carbon to produce the 1,3-diene 9.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Natural Products and Related Compounds using Enyne Metathesis

Mori

2007

Adv Synth Catal

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148

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Since the molybdenum and ruthenium carbene complexes 1a and 1b were discovered by Schrock and Grubbs in 1990 and 1992, synthetic organic chemistry has progressed with the use of these complexes as the catalyst for olefin metathesis. It was found that the ruthenium carbene complex was also effective for enyne metathesis, which occurs between an alkene and an alkyne. Intramolecular enyne metathesis gives various cyclic compounds having a 1,3-diene moiety and cross-metathesis of an alkene with an alkyne is a useful method for the synthesis of a compound having a diene moiety. Furthermore, dienyne metathesis, ROM of cycloalkenynes or tandem reactions of enyne metathesis have been developed. Using these various enyne metatheses, complicated natural products have been synthesized via novel routes. The syntheses of natural products and related compounds using enyne metathesis are described.

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“…Die geringe Ausbeute kçnnte auf die Koordination des N-Atoms an das Ruthenium im Cycloaddukt 78 zurückzuführen sein, da hierdurch eine Cycloreversion zu 79 unterbunden wird. [58] In letzter Zeit wurden ähnliche EthylenAlkin-Kreuzmetathesen zur Synthese einer Vielzahl von 1,3-Dien-haltigen Produkten verwendet. [59] 6.2.…”

Section: Ausbeuten Erhalten (Schema 22)unclassified

Übergangsmetallkatalysierte C‐C‐Kupplungen mit Ethylen im Labormaßstab

2013

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Ethylen ist das (volumenbezogen) in größter Menge synthetisierte organische Molekül. Es lässt sich leicht in übergangsmetallkatalysierte C‐C‐Kupplungsreaktionen einbinden, und zwar durch migratorische Insertion in Alkylmetall‐Intermediate. Wegen der D2h‐Symmetrie des Ethylens kann die Insertion nur einen einzigen Verlauf nehmen, was die Nebenproduktbildung limitiert und die Produktanalyse außerordentlich vereinfacht. Wie in diesem Kurzaufsatz beschrieben wird, wird bei vielen C‐C‐Kupplungen das Ethylenmolekül (oder mehrere) bei Umgebungsdruck und ‐temperatur eingefügt. Auch sind viele Reaktionen bekannt, bei denen ein in geeigneter Weise substituiertes Alken in das Produkt eingeführt wird.

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Novel 1,3-diene synthesis from alkyne and ethylene by ruthenium-catalyzed enyne metathesis

Cited by 100 publications

References 53 publications

Ruthenium vinyl carbene intermediates in enyne metathesis

Ruthenium vinyl carbene intermediates in enyne metathesis

Synthesis of Natural Products and Related Compounds using Enyne Metathesis

Übergangsmetallkatalysierte C‐C‐Kupplungen mit Ethylen im Labormaßstab

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