Transition metal complexes as catalysts of double-bond migration in O-allyl systems

Kuźnik, Nikodem; Krompiec, Stanisław

doi:10.1016/j.ccr.2006.07.006

Cited by 104 publications

(49 citation statements)

References 68 publications

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“…Ein Rhodium/Phosphoramidit-Katalysatorsystem ermög-lichte die enantioselektive Isomerisierung der Allylalkohole 321 [15,441,442] zu den chiralen Aldehyden 322 (Schema 101). [443] Mit dem Phosphoramidit-Liganden L51 wurden die Aldehyde 322 in hohen Ausbeuten und mit mittleren ee-Werten (bis 70 %) isoliert.…”

Section: Rhodiumkatalysierte Isomerisierung Von Allylalkoholenunclassified

Phosphoramidite: privilegierte Liganden in der asymmetrischen Katalyse

2010

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Die asymmetrische Katalyse mit Übergangsmetallkomplexen ist die Grundlage unzähliger stereoselektiver Umwandlungen und hat damit das Bild der modernen Synthesechemie gewandelt. Der Schlüssel zum Erfolg war die Entwicklung chiraler Liganden zur Kontrolle der Regio‐, Diastereo‐ und Enantioselektivität. Dabei haben sich Phosphoramidite als eine äußerst vielseitige und leicht zugängliche Klasse von chiralen Liganden erwiesen. Ihre modulare Struktur ermöglicht die Herstellung von Ligandenbibliotheken und erleichtert die Feinabstimmung für eine bestimmte katalytische Reaktion. Phosphoramidite bewirken oft außerordentlich hohe Stereoselektivitäten, und ihre einzähnige Natur ist in der kombinatorischen Katalyse, die gemischte Liganden verwendet, unverzichtbar. In diesem Aufsatz werden neue Entwicklungen in der asymmetrischen Katalyse mit Phosphoramiditen diskutiert, wobei der Schwerpunkt auf der Bildung von Kohlenstoff‐ Kohlenstoff‐ und Kohlenstoff‐Heteroatom‐Bindungen liegt.

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Section: Rhodiumkatalysierte Isomerisierung Von Allylalkoholenunclassified

Phosphoramidite: privilegierte Liganden in der asymmetrischen Katalyse

2010

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“…Unfortunately,R CM of ester 3 formed from renewable oleic acid derived 1 and 2 leads to al arge, 19membered macrocycle 4 of rather weak [16,17] odour (Scheme 1). Therefore, we opted to search for ap rocedure that allows for formation of more pleasantly odoured 15 to 18-membered musksf rom renewable 9-DA.R ing sizes could be tailored only if selective alkene isomerization [17][18][19] followed by RCM could be achieved. Because alkene isomerization and metathesis reactions are both very importantt ools in organic chemistry,d evel-oping ways of linking them in as equence is of great importance.…”

Section: Introductionmentioning

confidence: 99%

Sequential Alkene Isomerization and Ring‐Closing Metathesis in Production of Macrocyclic Musks from Biomass

Sytniczuk

Forcher

Grotjahn

et al. 2018

Chemistry A European J

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We report successful utilization of sequential alkene isomerization and ring-closing metathesis of dec-9-enoic acid based dienes in synthesis of macrocyclic lactones that possess a strong scent of musk. This catalytic sequence was essential to trim the chain length of starting dienes to yield macrocycles of the right size. Dec-9-enoic acid is conveniently obtainable from oleic esters by Ru-catalysed ethenolysis.

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“…Additionally, these methods are often used in the pharmaceutical and fragrance industry. [23][24][25][26][27] As early as 1966, Frankel et al described the isomerization activity of simple iron pentacarbonyl complexes. Hence, mixtures of olefins are obtained, and the selective functionalization of such mixtures continues to be a highly challenging task.…”

Section: Introductionmentioning

confidence: 99%

Benign Catalysis with Iron: Unique Selectivity in Catalytic Isomerization Reactions of Olefins

et al. 2012

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The use of noble metal catalysts in homogeneous catalysis has been well established. Due to their price and limited availability, there is growing interest in the substitution of such precious metal complexes with readily available and bio-relevant catalysts. In particular, iron is a "rising star" in catalysis. Herein, we present a general and selective iron-catalyzed monoisomerization of olefins, which allows for the selective generation of 2-olefins. Typically, common metal complexes give mixtures of various internal olefins. Both bulk-scale terminal olefins and functionalized terminal olefins give the corresponding products under mild conditions in good to excellent yields. The proposed reaction mechanism was elucidated by in situ NMR studies and supported by DFT calculations and extended X-ray absorption fine structure (EXAFS) measurements.

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Transition metal complexes as catalysts of double-bond migration in O-allyl systems

Cited by 104 publications

References 68 publications

Phosphoramidite: privilegierte Liganden in der asymmetrischen Katalyse

Phosphoramidite: privilegierte Liganden in der asymmetrischen Katalyse

Sequential Alkene Isomerization and Ring‐Closing Metathesis in Production of Macrocyclic Musks from Biomass

Benign Catalysis with Iron: Unique Selectivity in Catalytic Isomerization Reactions of Olefins

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