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Bücher Englische Bücher Wissen & Bildung Naturwissenschaft, Medizin, Informatik, Technik Chemie Organische Chemie Enantioselective Photocatalysis: Alkene Deracemization and [2pi+2sigma] Photocycloadditions Enabled by Triplet Energy Transfer
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Enantioselective Photocatalysis: Alkene Deracemization and [2pi+2sigma] Photocycloadditions Enabled by Triplet Energy Transfer
Thilo Kratz (Broschiert, Englisch)
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Beschreibung
Photochemical deracemization allows the conversion of a racemic mixture into a single enantiomer without the loss of material. This can be achieved by isomerization of the respective molecules. The aim of this dissertation was the design of alkene substrates suitable for enantioselective E/Z-isomerization enabled by triplet energy transfer. A concise synthesis of tetrasubstituted alkenes was… developed and axially chiral alkenes were obtained in moderate to good yields. The developed method was applicable for various cyclic ketones. Subsequent photochemical deracemization employing a chiral thioxanthone sensitizer produced the axially chiral alkenes with high enantioselectivities and good yields. Dilution experiments monitored by 1H NMR revealed different strength of association of the substrate enantiomers to the catalyst whereupon a mechanism for the triplet sensitized alkene deracemization was proposed. Additionally, the well established [2π+2π] photocycloaddition was extended by photocycloaddition of highly ring strained bicyclo[1.1.0]butanes allowing the synthesis of complex, three dimensional molecular structures. The [2π+2σ] photocycloaddition of bicyclo[1.1.0]butanes with quinolones and other heterocycles was examined with the goal to develop an enantioselective reaction. Various 3- and 4-substituted quinolones underwent sensitized [2π+2σ] photocycloaddition with a selected bicyclo[1.1.0]butane in good yields. First results of an enantioslective [2π+2σ] photocycloaddition with bicyclo[1.1.0]butanes were already promising with enantioselectivities up to 73%. Dieses Produkt haben wir gerade leider nicht auf Lager.
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Technische Daten
Erscheinungsdatum
30.06.2024
Sprache
Englisch
EAN
9783843953542
Herausgeber
Dr. Hut
Serien- oder Bandtitel
Organische Chemie
Sonderedition
Nein
Autor
Thilo Kratz
Seitenanzahl
190
Einbandart
Broschiert
Schlagwörter
Enantioselective Catalysis, Photocatalysis, Sensitization
Thema-Inhalt
PNN - Organische Chemie
Höhe
210 mm
Breite
14.8 cm
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