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Jacobsen's catalysts R = Alkyl, O-alkyl, O-trialkyl Best Jacobsen catalyst: R = t Bu Katsuki's catalysts R 1 = Aryl, substituted aryl R 2 = Aryl, Alkyl. The Jacobsen epoxidation, sometimes also referred to as Jacobsen-Katsuki epoxidation is a chemical reaction which allows enantioselective epoxidation of unfunctionalized alkyl- and aryl- substituted alkenes.
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Both enantiomers of Jacobsen's catalyst are commercially available. Jacobsen's catalyst can be prepared by separating 1,2-diaminocyclohexane into its component enantiomers and then reacting the appropriate tartrate with 3,5-di-tert-butyl-2-hydroxybenzaldehyde to form a Schiff base (see intermediate formed in the reaction scheme below).
See below for a survey of the substrate scope of the reaction. When chiral, non-racemic peroxides are used, the two transition states of epoxidation leading to enantiomeric products are diastereomeric. Steric interactions between the peroxide, enone, and templating cation M + influence the sense of selectivity observed. [9] (3)
This template was developed to handle the reaction ontologies as e.g. developed by the RSC (Royal Society of Chemistry). A representation of the ontology is shown in the picture on the right. A representation of the ontology is shown in the picture on the right.
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