Organocatalytic Approaches to Asymmetric Oxidation Epoxidation of -Branched Enals and -Benzoyloxylation of Carbonyl Compounds
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- Englisch ausgewählt
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Beschreibung
Produktdetails
Einband
Taschenbuch
Erscheinungsdatum
08.05.2015
Verlag
LAP LAMBERT Academic PublishingSeitenzahl
256
Maße (L/B/H)
22/15/1.6 cm
Gewicht
399 g
Sprache
Englisch
ISBN
978-3-659-69254-3
This work describes the development of enantioselective oxidation reactions of carbonyl compounds using covalent organocatalysis. In the first part, asymmetric epoxidation of a-branched a,ss-unsaturated aldehydes with aqueous hydrogen peroxide is presented. An exceptionally synergistic combination of a primary cinchona alkaloid-derived amine and a chiral BINOL-derived phosphoric acid was found to promote the reaction with excellent enantiocontrol for a wide variety of a,ss-disubstituted and a-monosubstituted enals. Conformational analysis of catalytically relevant intermediates using NMR and computational techniques enabled the rationalization of the absolute stereochemistry of products. The second part of this book describes a highly efficient direct catalytic asymmetric a-benzoyloxylation of cyclic ketones. The same primary amine paired with an inorganic acid was found to be an effective catalyst for a wide range of substrates. The methodology was applied to the first asymmetric synthesis of (+)-2ss,4-dihydroxy-1,8-cineole, a predicted terpenoid metabolite in mammals.
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