Epoxidations and Hydroperoxidations of α,β-Unsaturated Ketones

An Approach through Asymmetric Organocatalysis

  • Corinna Reisinger

Part of the Springer Theses book series (Springer Theses)

Table of contents

  1. Front Matter
    Pages i-xv
  2. Corinna Reisinger
    Pages 1-3
  3. Corinna Reisinger
    Pages 5-40
  4. Corinna Reisinger
    Pages 41-43
  5. Corinna Reisinger
    Pages 45-139
  6. Corinna Reisinger
    Pages 141-146
  7. Corinna Reisinger
    Pages 147-151
  8. Corinna Reisinger
    Pages 153-255
  9. Back Matter
    Pages 257-257

About this book

Introduction

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.

Keywords

Asymmetric counteranion-directed catalysis Asymmetric peroxidation reactions Asymmetric synthesis of epoxy ketones Cinchona alkaloid derivatives as organocatalysts Organocatalytic epoxidation of unsaturated ketones

Authors and affiliations

  • Corinna Reisinger
    • 1
  1. 1.Evonik AGHanau-WolfgangGermany

Bibliographic information

  • DOI https://doi.org/10.1007/978-3-642-28118-1
  • Copyright Information Springer-Verlag Berlin Heidelberg 2012
  • Publisher Name Springer, Berlin, Heidelberg
  • eBook Packages Chemistry and Materials Science
  • Print ISBN 978-3-642-28117-4
  • Online ISBN 978-3-642-28118-1
  • Series Print ISSN 2190-5053
  • Series Online ISSN 2190-5061
  • About this book