1998
DOI: 10.1016/s0957-4166(98)00023-8
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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))

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Cited by 24 publications
(10 citation statements)
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“…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%
“…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%
“…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%
“…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