Ring closing diene metathesis in organic synthesis

Armstrong, S. K.

doi:10.1039/a703881j

Cited by 596 publications

(118 citation statements)

References 70 publications

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“…We expected this new material to amplify the recyclability, or activate differently the aryl halides. In these reports, we have presented the following findings: 1) a {Pd}-S-GaAs(001) plate catalyzed the Heck reaction more efficiently than Pd(PPh 3 ) 4 , which is widely used as a homogeneous catalyst, and could be reused at least 10 times, 2) inactivated {Pd}-S-GaAs(001) could be revitalized by further treatment with Pd(PPh 3 ) 4 , and 3) sulfur-termination in this catalyst was important for stability of this catalyst. 135,136) Here, we present a method for preparing {Pd}-SGaAs(001), which is drastically improved in both catalytic activity and stability.…”

Section: Development Of Palladium Catalyst Supported On Gaas(001): Bmentioning

confidence: 93%

“…4) Gesson and co-workers successfully applied RCM to 11-membered lactones from carbohydrate derivatives. 52) As shown in Chart 3, azacycloundecene compounds (16 or 17), which are key intermediates in our syntheses of 12 and 13, were prepared by cyclization of the ditosylates 15 derived from the corresponding alkyne.…”

Section: Mitsuhiro Arisawa Was Born In 1971 Inmentioning

confidence: 99%

“…In this field, ruthenium carbene catalysts have received much attention and are frequently used in the synthesis of biologically active natural products, because of their stability, functional group tolerance, easy handling and commercial availability. [1][2][3][4] Over the past decades, well-defined ruthenium catalysts have been developed and Grubbs et al reported the first practical catalyst (D). 5,6) The recent introduction of catalysts (E, 7-9) G 10) ) bearing N-heterocyclic carbene (NHC) ligand has led to much higher reactivity (Fig.…”

Section: Development Of Syntheticmentioning

confidence: 99%

“…The overall procedure consisted of the RCM reaction of chiral dienes (1)(2)(3)(4)(5) in the presence of catalyst (C, D) to form the corresponding bicyclic lactam (6-9) ( Table 1). Dienes 1-5 were prepared from L-proline in good yield and subjected to RCM.…”

Section: Development Of Syntheticmentioning

confidence: 99%

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Development of Environmentally Benign Organometallic Catalysis for Drug Discovery and Its Application

Arisawa

2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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We have developed a novel organometallic catalysis and applied it to drug discovery. Two new catalysts were found, ruthenium hydride with a nitrogen-containing heterocyclic carbene (A) and an organopalladium catalyst supported on a sulfur-terminated semiconductor, gallium arsenide (001) (B). Both catalysts are environmentally benign, because A can yield indole derivatives with good atom economy, and B can catalyze the Mizoroki-Heck reaction more than 10 times with only trace amounts of leached palladium (ppb level). We also describe our synthetic study of nitrogen-containing heterocycles using ring-closing metathesis (RCM), such as chiral bicyclic lactams, azacycloundecenes, axially chiral macrolactams, 1,2-dihydroquinolines and indoles, including the development of silyl-enol ether ene metathesis, selective isomerization of terminal olefin, enamide metathesis and cycloisomerization and its application to the syntheis of 4 natural products, (؊)-coniceine, (S)-pyrrolam A, angustureine, and fistulosin.

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Section: Development Of Palladium Catalyst Supported On Gaas(001): Bmentioning

confidence: 93%

Section: Mitsuhiro Arisawa Was Born In 1971 Inmentioning

confidence: 99%

Section: Development Of Syntheticmentioning

confidence: 99%

Section: Development Of Syntheticmentioning

confidence: 99%

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Development of Environmentally Benign Organometallic Catalysis for Drug Discovery and Its Application

Arisawa

2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…A perspectiva mais concreta é a constante descoberta de novos catalisadores cada vez mais ativos, eficientes e seletivos, e ainda estáveis, para executar reações cada vez mais exigentes, porém em condições experimentais simples. Uma bibliografia geral apresentada [71][72][73][74][75][76][77][78][79][80][81][82][83][84] inclui revisões pertinentes, que servem como base para conhecer melhor esta reação tão importante em química orgânica.…”

Section: Conclusão E Perspectivasunclassified

A reação de metátese de olefinas: reorganização e ciclização de compostos orgânicos

Frederico¹,

Brocksom²,

Brocksom³

2005

Quím. Nova

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Recebido em 12/7/04; aceito em 13/10/04; publicado na web em 4/2/05 THE OLEFIN METATHESIS REACTION: REORGANIZATION AND CICLIZATION OF ORGANIC COMPOUNDS. The olefin metathesis reaction allows the exchange of complex alkyl units between two olefins, with the formation of a new olefinic link and a sub-product olefin usually ethylene. This reaction has found extensive application in the last ten years with the development of the Grubbs and Schrock catalysts, in total synthesis of complex organic molecules, as opposed to the very important use in the petrochemical industry with relatively simple molecules. This review intends to trace a historical and mechanistic pathway from industry to academy, before illustrating the more recent advances.Keywords: olefin metathesis; ring-closing metathesis; cross metathesis. No sentido químico, a palavra metátese descreve, por tradução direta do grego "troca de posição", a troca de ligações covalentes entre dois alcenos (ou olefinas) ou entre um alceno e um alcino. Na química de olefinas, ela se refere a uma redistribuição do esqueleto carbônico (Esquema 1), no qual ligações duplas carbono-carbono são rearranjadas na presença de um complexo metal-carbeno, representando um método catalítico de quebra e de formação de ligações múltiplas carbono-carbono. Esta reação é conhecida na petroquímica e na química dos polímeros há mais de 40 anos 1 , mas só na década de noventa, com o advento de novos e eficientes catalisadores, desenvolvidos principalmente pelos grupos de pesquisa de Schrock 2,3 e Grubbs 4,5 , ela emergiu como uma potente ferramenta na química orgânica acadêmica. INTRODUÇÃOEstes novos catalisadores proporcionaram um grande aumento no número de aplicações desta reação, atraindo a atenção de quí-micos acadêmicos e industriais. Atualmente, estas aplicações estão relacionadas com a metátese entre dois alcenos (metátese de dienos) ou entre um alceno e um alcino (metátese de eninos) mostradas no Esquema 2.A reação entre duas olefinas distintas recebe o nome de metátese cruzada (CM do inglês "cross-metathesis") e a sua versão intramolecular, a reação entre duas ligações duplas na mesma molécula, é conhecida como metátese de fechamento de anel (RCM; "ring-closing metathesis"). A formação de dienos não conjugados a partir de olefinas cíclicas é conhecida por abertura de anel por metátese (ROM; "ring-opening metathesis") e, formalmente é a reação inversa da RCM. Reações de polimerização podem ocorrer entre dienos acíclicos (ADMET; "acyclic diene metathesis polymerization") ou ainda com alcenos cíclicos, através do processo de abertura de anel por metátese (ROMP; "ring-opening metathesis polymerization"). As combinações dos processos de CM, RCM e ROM deram origem a uma nova e eficiente estratégia para

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Der Stand der Totalsynthese zu Beginn des 21. Jahrhunderts

Nicolaou¹,

et al. 2000

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Ein neues Jahrtausend hat begonnen – Grund genug, sich die Frage zu stellen, welchen Stand die Totalsynthese von Naturstoffen erreicht hat. Dieser Aufsatz möchte eine Antwort geben, indem er die Entwicklung dieser chemischen Disziplin, die Aspekte von exakter Wissenschaft und schöner Kunst in sich vereint, von Anbeginn bis in die heutige Zeit beschreibt; es wird geschildert, wie viel wir in der Wissenschaft der Totalsynthese schon erreicht haben, aber auch, dass dieses Forschungsgebiet den Kinderschuhen gerade erst entschlüpft.

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Ring closing diene metathesis in organic synthesis

Cited by 596 publications

References 70 publications

Development of Environmentally Benign Organometallic Catalysis for Drug Discovery and Its Application

Development of Environmentally Benign Organometallic Catalysis for Drug Discovery and Its Application

A reação de metátese de olefinas: reorganização e ciclização de compostos orgânicos

Der Stand der Totalsynthese zu Beginn des 21. Jahrhunderts

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