Overview

Corinna Reisinger has developed a new organocatalytic asymmetric epoxidation of cyclic and acyclic α,β-unsaturated ketones. In this thesis, Corinna documents her methodology, using primary amine salts as catalysts, and hydrogen peroxide as an inexpensive and environmentally benign oxidant. She describes the unprecedented and powerful catalytic asymmetric hydro­peroxi­dation of α,β-enones, a process which produces optically active five-membered cyclic peroxyhemiketals in a single operation. She also proves the versatility and synthetic value of the cyclic peroxyhemiketals by converting them into highly enantioenriched acyclic and cyclic aldol products. Currently, these cyclic aldol products are inaccessible by any other synthetic means. Furthermore, cyclic peroxyhemiketals are precursors to optically active 1,2-dioxolanes which are of biological relevance. This work is a breakthrough in the field of asymmetric epoxidation chemistry and outlines the most efficient method in the literature for generating highly enantioselective cyclic epoxyketones known to date.

Full Product Details

Author:   Corinna Reisinger
Publisher:   Springer-Verlag Berlin and Heidelberg GmbH & Co. KG
Imprint:   Springer-Verlag Berlin and Heidelberg GmbH & Co. K
Edition:   2012 ed.
Dimensions:   Width: 15.50cm , Height: 1.50cm , Length: 23.50cm
Weight:   0.427kg
ISBN:  

9783642435331

ISBN 10:   3642435335
Pages:   260
Publication Date:   18 July 2014
Audience:   College/higher education ,  Professional and scholarly ,  Postgraduate, Research & Scholarly ,  Professional & Vocational
Format:   Paperback
Publisher's Status:   Active
Availability:   Manufactured on demand  
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Table of Contents

Background.- Asymmetric Organocatalysis.- Catalytic Asymmetric Epoxidation of Electron-Deficient Olefins.- Synthesis and Relevance of 3-Hydroxy-1,2-dioxolanes and 1,2-Dioxolanes.- Objectives of this Ph.D. Work.- Results and Discussion.- Catalytic Asymmetric Epoxidation of Cyclic Enones.- Catalytic Asymmetric Epoxidation and Hydroperoxidation of Acyclic Enones.- Synthetic Transformations of Optically Active a,ß-Epoxy Ketones and 3-Hydroxy-1,2-dioxolanes.- Summary and Conclusions.- Mechanistic Considerations.- Preparation of Starting Materials.- Catalyst Synthesis.- Summary.- Outlook.- Experimental Part.- General Experimental Conditions.- Catalytic Asymmetric Epoxidation of Cyclic Enones.- Catalytic Asymmetric Hydroperoxidation and Epoxidation of Acyclic Enones.- Synthetic Transformations of Optically Active Products.- Preparation of Starting Materials.- Catalyst Synthesis.

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