A Short Route to α‐Tocopherol

Liu, Kegang; Chougnet, Antoinette; Woggon, Wolf‐D.

doi:10.1002/ange.200801765

Cited by 64 publications

(17 citation statements)

References 64 publications

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“…Biomimetic routes for chromanol cyclization have been developed on the basis of these data. [222,223] Organocatalytic [224] and other approaches [225][226][227][228] based on new synthetic methods have also been published in recent years, thus showing that the synthesis of RRR-92 is still a research topic of current interest.…”

Section: Angewandte Chemiementioning

confidence: 99%

One Hundred Years of Vitamins—A Success Story of the Natural Sciences

Eggersdorfer¹,

Laudert²,

Létinois³

et al. 2012

Angew Chem Int Ed

265

209

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The discovery of vitamins as essential factors in the diet was a scientific breakthrough that changed the world. Diseases such as scurvy, rickets, beriberi, and pellagra were recognized to be curable with an adequate diet. These diseases had been prevalent for thousands of years and had a dramatic impact on societies as well as on economic development. This Review highlights the key achievements in the development of industrial processes for the manufacture of eight of the 13 vitamins.

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Section: Angewandte Chemiementioning

confidence: 99%

One Hundred Years of Vitamins—A Success Story of the Natural Sciences

Eggersdorfer¹,

Laudert²,

Létinois³

et al. 2012

Angew Chem Int Ed

265

209

View full text Add to dashboard Cite

show abstract

“…1). In spite of the potential to address important synthetic issues, such as the effective catalytic generation of a new carbon-carbon bond and a new stereocenter γ to a carbonyl group, dienamine catalysis has found limited application (28,29). Accordingly, a recently published perspective on the advent of organocatalysis did not include dienamine catalysis among the generic modes of activation and induction (30).…”

Section: Microbiologymentioning

confidence: 99%

Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis

Bencivenni

Galzerano

Mazzanti

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

186

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In spite of the many catalytic methodologies available for the asymmetric functionalization of carbonyl compounds at their α and β positions, little progress has been achieved in the enantioselective carbon–carbon bond formation γ to a carbonyl group. Here, we show that primary amine catalysis provides an efficient way to address this synthetic issue, promoting vinylogous nucleophilicity upon selective activation of unmodified cyclic α,β-unsaturated ketones. Specifically, we document the development of the unprecedented direct and vinylogous Michael addition of β-substituted cyclohexenone derivatives to nitroalkenes proceeding under dienamine catalysis. Besides enforcing high levels of diastereo- and enantioselectivity, chiral primary amine catalysts derived from natural cinchona alkaloids ensure complete γ-site selectivity: The resulting, highly functionalized vinylogous Michael adducts, having two stereocenters at the γ and δ positions, are synthesized with very high fidelity. Finally, we describe the extension of the dienamine catalysis-induced vinylogous nucleophilicity to the asymmetric γ-amination of cyclohexene carbaldehyde.

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“…[222,223] Zudem wurden in den letzten Jahren organokatalytische [224] und andere Zugänge [225][226][227][228] unter Verwendung neuer Synthesemethoden verçffentlicht. [222,223] Zudem wurden in den letzten Jahren organokatalytische [224] und andere Zugänge [225][226][227][228] unter Verwendung neuer Synthesemethoden verçffentlicht.…”

Section: Methodsunclassified

“…Auf Grundlage dieser Erkenntnisse wurden biomimetische Routen für den Chromanolringschluss entwickelt. [222,223] Zudem wurden in den letzten Jahren organokatalytische [224] und andere Zugänge [225][226][227][228] unter Verwendung neuer Synthesemethoden verçffentlicht. Dies zeigt, dass die Synthese von RRR-92 noch immer ein aktuelles Forschungsthema ist.…”

Section: Methodsunclassified

Einhundert Jahre Vitamine – eine naturwissenschaftliche Erfolgsgeschichte

et al. 2012

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Die Entdeckung der Vitamine als lebenswichtige Verbindungen in der Nahrung vor 100 Jahren stellte einen wissenschaftlichen Durchbruch dar, der die Welt veränderte. Die Erkenntnis, dass sich früher weit verbreitete Krankheiten wie Skorbut, Pellagra, Rachitis und Beriberi durch eine ausgewogene Ernährung vermeiden oder heilen lassen, hatte einschneidende Auswirkungen auf Gesellschaft und wirtschaftliche Entwicklung. Dieser Aufsatz fasst Schlüsselerfolge in Entwicklung und industrieller Herstellung von acht der insgesamt dreizehn Vitamine zusammen.

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A Short Route to α‐Tocopherol

Abstract: Ganz einfach: Ein einfacher und praktischer Zugang zu α‐Tocopherol wird vorgestellt (siehe Schema; TES=Triethylsilyl). Schlüsselschritt ist eine durch das Prolinderivat 1 geförderte, bemerkenswert diastereoselektive Aldol‐Oxa‐Michael‐Dominoreaktion.

Cited by 64 publications

References 64 publications

One Hundred Years of Vitamins—A Success Story of the Natural Sciences

One Hundred Years of Vitamins—A Success Story of the Natural Sciences

Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis

Einhundert Jahre Vitamine – eine naturwissenschaftliche Erfolgsgeschichte

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