Amplification of chirality by transition metal coordination: synthesis of chiral allenes and allene manganese complexes of high enantiomeric purity. Synthesis of methyl ( R , E )-(−)-(2,4,5-tetradecatrienoate (pheromone of Acanthoscelides obtectus (say))

Franck‐Neumann, M.; Martina, Daniel; Neff, Denis

doi:10.1016/s0957-4166(98)00023-8

Cited by 24 publications

(10 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Whereas Satoh et al [23] benefited from the stereoselective replacement of a chiral sulfinyl group using a magnesium organometallic followed by subsequent elimination for the generation of both enantiomers of 12 with about 80 % ee, Franck-Neumann and coworkers [24] utilized the manganese complex 13 (formed by deracemization) to obtain the enantiomerically pure target molecule 12 by Horner-Wadsworth-Emmons olefination and oxidative decomplexation of the intermediate vinylallene complex 14 (Scheme 6).…”

Section: Linear Allenesmentioning

confidence: 99%

Synthesis and Properties of Allenic Natural Products and Pharmaceuticals

2004

View full text Add to dashboard Cite

Nowadays, about 150 natural products comprising an allenic or cumulenic structure are known. The chemistry of these compounds has turned out to be a very attractive and prolific area of interest: advances in the isolation and characterization of new allenic natural products have led to the establishment of efficient synthetic procedures which in many cases also open up an access to enantiomerically pure target molecules. Inspired by the intriguing biological activities of many allenic natural products, allene moieties are now systematically introduced in pharmacologically active classes of compounds (steroids, prostaglandins, amino acids, nucleosides). The functionalized allenes thus obtained often exhibit impressive activities as mechanism-based enzyme inhibitors, cytotoxic, or antiviral agents. A prerequisite for further developments in this field is the efficient stereoselective synthesis of allene derivatives.

show abstract

Section: Linear Allenesmentioning

confidence: 99%

Synthesis and Properties of Allenic Natural Products and Pharmaceuticals

2004

View full text Add to dashboard Cite

show abstract

“…Hydrazone 40 was hydrolyzed in good yield to reveal enantiomerically enriched allenal 41 . Further elaboration of 41 led to the synthesis of insect pheromone 42 in high enantiomeric purity [34].…”

Section: Manganese Auxiliariesmentioning

confidence: 99%

Carbon-Carbon Bond Formation Facilitated by π-Complexed Organometallic Auxiliaries: An Overview

Roy

Bhat

Lepore

2019

LOC

View full text Add to dashboard Cite

A Review: Organometallic moieties attached to substrates via π-complexation play an important role as auxiliaries. As described in the present review, η-linked auxiliaries have been employed to overcome numerous synthesis obstacles that continue to present significant challenges for catalyzed reactions. This has been particularly true in carbon-carbon bond forming reactions involving highly unsaturated systems such as arenes, dienes and allenes, which are emphasized here.

show abstract

“…Während Satoh et al23 durch den Austausch einer chiralen Sulfinylfunktion gegen Magnesium mit anschließender Eliminierung beide Enantiomere von 12 mit ca. 80 % ee erhielten, verwendeten Franck‐Neumann und Mitarbeiter24 den mittels Racematspaltung gewonnenen Mangankomplex 13 zur Synthese der enantiomerenreinen Zielverbindung 12 durch Horner‐Wadsworth‐Emmons‐Olefinierung und anschließende oxidative Dekomplexierung des Vinylallen‐Komplexes 14 (Schema ).…”

Section: Allenische Naturstoffeunclassified

Synthese und Eigenschaften allenischer Natur‐ und Wirkstoffe

2004

View full text Add to dashboard Cite

Heute sind etwa 150 Naturstoffe mit Allen‐ oder Cumulen‐Struktur bekannt. Die Chemie dieser Verbindungen hat sich als ein reizvolles und fruchtbares Gebiet erwiesen: Fortschritte in der Isolierung und Charakterisierung neuer allenischer Naturstoffe haben zur Etablierung effizienter Syntheseverfahren geführt, die häufig einen Zugang zu enantiomerenreinen Produkten eröffneten. Wegen der oftmals beeindruckenden biologischen Eigenschaften allenischer Naturstoffe sind Allengruppierungen mittlerweile systematisch in pharmakologisch aktive Verbindungsklassen (Steroide, Prostaglandine, Aminosäuren, Nucleoside) eingebaut worden. Diese funktionalisierten Allene weisen in vielen Fällen interessante Aktivitäten auf, beispielsweise als Mechanismus‐inhärente Enzyminhibitoren, Cytostatika oder antivirale Wirkstoffe. Eine grundlegende Voraussetzung für weitere Entwicklungen auf diesem Gebiet ist die effiziente stereoselektive Synthese von Allenderivaten.

show abstract

Amplification of chirality by transition metal coordination: synthesis of chiral allenes and allene manganese complexes of high enantiomeric purity. Synthesis of methyl ( R , E )-(−)-(2,4,5-tetradecatrienoate (pheromone of Acanthoscelides obtectus (say))

Cited by 24 publications

References 13 publications

Synthesis and Properties of Allenic Natural Products and Pharmaceuticals

Synthesis and Properties of Allenic Natural Products and Pharmaceuticals

Carbon-Carbon Bond Formation Facilitated by π-Complexed Organometallic Auxiliaries: An Overview

Synthese und Eigenschaften allenischer Natur‐ und Wirkstoffe

Contact Info

Product

Resources

About