1,2‐Epoxycarotinoide 5. Mitteilung, Synthese von (<i>S</i>)‐1,2‐Epoxy‐1,2,7,8,7′,8′‐hexahydro‐Ψ, Ψ‐carotin ((<i>S</i>)‐1,2‐Epoxy‐1,2‐dihydro‐ζ‐carotin)

Arm, Christoph; Pfander, Hanspeter

doi:10.1002/hlca.19840670619

Cited by 9 publications

References 10 publications

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Asymmetric Epoxidation of Allylic Alcohols: the Katsuki–Sharpless Epoxidation Reaction

1996

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In 1980, Sharpless and Katsuki discovered a system for the asymmetric epoxidation of primary allylic alcohols that utilizes Ti(OPr‐ i ) 4 , a dialkyl tartrate as a chiral ligand, and tert ‐butyl hydroperoxide as the oxidant. Notably, this reaction exhibits high levels of enantioselectivity (usually > 90% ee). Like other metal‐catalyzed epoxidations, this reaction also proceeds under mild conditions with good chemical yield and with high regio‐ and chemoselectivity. Various aspects of this reaction, including its mechanism, early synthetic applications, and further transformations of the epoxy alcohol product, have been reviewed. In this chapter, the full scope and limitations of this reaction, its synthetic applications, and typical experimental conditions are described.

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Asymmetric Epoxidation of Allylic Alcohols: the Katsuki–Sharpless Epoxidation Reaction

1996

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ChemInform Abstract: 1,2‐EPOXYCAROTENOIDS. 5. SYNTHESIS OF (S)‐1,2‐EPOXY‐1,2,7,8,7′,8′‐HEXAHYDRO‐Ψ,Ψ‐CAROTENE ((S)‐1,2‐EPOXY‐1,2‐DIHYDRO‐ζ‐CAROTENE)

Pfander¹

1984

Chemischer Informationsdienst

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Optisch aktive Lycopin‐epoxide und Lycopin‐glycole: Synthesen und chiroptische Eigenschaften

Meier

Uebelhart

Eugster

1986

Helvetica Chimica Acta

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Optically Active Lycopene Epoxides and Lycopene Glycols: Synthesis and Chiroptical PropertiesWe present extensive spectral and chiroptical data on the pure and crystalline lycopene diepoxides 1-3 and glycols 6 9 . A first synthetic approach to 1-9 with (+)-malic acid as starting material afforded 30 as a complex mixture of isomers (Scheme I ) . Pure stereoisomers 1-9 were obtained using the enantiomerically pure epoxygeraniol 31 as starting material (Scheme 2). Differentiation of the (5Z)-from the (all-E)-isomers by 'H-NMR and UVjVIS alone is very difficult.1. Einleitung. -Die absolute Konfiguration eines acyclischen optisch aktiven Carotinoids lasst sich auch heute noch nicht mit Sicherheit aus CD-Daten allein herleiten, da sich scheinbar geringfugige strukturelle Anderungen in der weiteren Umgebung eines Chiralitltszentrums in unerwarteter Weise auf die Cotton -Effekte auswirken konnen.

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1,2‐Epoxycarotinoide 5. Mitteilung, Synthese von (S)‐1,2‐Epoxy‐1,2,7,8,7′,8′‐hexahydro‐Ψ, Ψ‐carotin ((S)‐1,2‐Epoxy‐1,2‐dihydro‐ζ‐carotin)

Cited by 9 publications

References 10 publications

Asymmetric Epoxidation of Allylic Alcohols: the Katsuki–Sharpless Epoxidation Reaction

Asymmetric Epoxidation of Allylic Alcohols: the Katsuki–Sharpless Epoxidation Reaction

ChemInform Abstract: 1,2‐EPOXYCAROTENOIDS. 5. SYNTHESIS OF (S)‐1,2‐EPOXY‐1,2,7,8,7′,8′‐HEXAHYDRO‐Ψ,Ψ‐CAROTENE ((S)‐1,2‐EPOXY‐1,2‐DIHYDRO‐ζ‐CAROTENE)

Optisch aktive Lycopin‐epoxide und Lycopin‐glycole: Synthesen und chiroptische Eigenschaften

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