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Selectivity in the Synthesis of Cyclic Sulfonamides

Application in the Synthesis of Natural Products

  • Book
  • © 2014

Overview

Authors:
  1. Kimberly Geoghegan

    1. HCI F 308, ETH Zürich, Zürich, Switzerland

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  • Nominated as an Outstanding Ph.D. thesis by the University College Dublin, Ireland
  • Development of new methodology combined with target synthesis
  • Experimental details provided for all transformations-including unpublished results and procedures
  • Includes supplementary material: sn.pub/extras

Part of the book series: Springer Theses (Springer Theses)

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Table of contents (6 chapters)

  1. Front Matter

    Pages i-xiii
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  2. Introduction

    • Kimberly Geoghegan
    Pages 1-15

  3. Regioselectivity in the Heck (Mizoroki-Heck) Reaction

    • Kimberly Geoghegan
    Pages 17-41

  4. Wagner-Meerwein Rearrangement of Cyclic Sulfonamides

    • Kimberly Geoghegan
    Pages 43-54

  5. An Investigation into the One-Pot Heck Olefination-Hydrogenation Reaction

    • Kimberly Geoghegan
    Pages 55-65

  6. Double Reduction of Cyclic Aromatic Sulfonamides

    • Kimberly Geoghegan
    Pages 67-79

  7. Experimental

    • Kimberly Geoghegan
    Pages 81-141

  8. Back Matter

    Pages 143-151
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Keywords

About this book

In the area of organic chemistry one major challenge we are currently faced with is how to assemble potentially useful molecules in new ways that generate molecular complexity and in sequences that are as efficient as possible. Our efforts in this regard, specifically for the preparation of amino containing compounds incorporating an aromatic ring, are described in this doctoral thesis. We discovered an interesting regioselectivity in an intramolecular Heck reaction, which we studied for a series of substrates that are unbiased in terms of the size of the newly formed ring, where very high levels of selectivity in relation to the new carbon-carbon bond are typically observed. DFT calculations were performed to attempt to shed light on the reaction sequence. This regioselective Heck reaction, combined with the reductive removal of the temporary amino-protecting group, allowed us to synthesize the Sceletium alkaloids: mesembrane, mesembranol and mesembrine.

Authors and Affiliations

  • HCI F 308, ETH Zürich, Zürich, Switzerland

    Kimberly Geoghegan

About the author

Kimberly Geoghegan graduated from University College Dublin (UCD) with a B.Sc. in Chemistry in 2009.  She continued on in UCD and joined the research group of Dr. Paul Evans.  She was awarded a National University of Ireland (NUI) Travelling Studentship to undertake her doctoral studies on the regioselective Heck reaction and its applications in the synthesis of natural products, and graduated with her Ph.D. in 2013.  Since 2014, Kimberly has been a postdoctoral researcher in the group of Prof. Jeffrey W. Bode at ETH Zürich, where she is developing novel reagents for the synthesis of saturated nitrogen containing heterocycles.

Bibliographic Information

  • Book Title: Selectivity in the Synthesis of Cyclic Sulfonamides

  • Book Subtitle: Application in the Synthesis of Natural Products

  • Authors: Kimberly Geoghegan

  • Series Title: Springer Theses

  • DOI: https://doi.org/10.1007/978-3-319-10338-9

  • Publisher: Springer Cham

  • eBook Packages: Chemistry and Materials Science, Chemistry and Material Science (R0)

  • Copyright Information: Springer International Publishing Switzerland 2014

  • Hardcover ISBN: 978-3-319-10337-2Published: 03 September 2014

  • Softcover ISBN: 978-3-319-36431-5Published: 23 August 2016

  • eBook ISBN: 978-3-319-10338-9Published: 20 August 2014

  • Series ISSN: 2190-5053

  • Series E-ISSN: 2190-5061

  • Edition Number: 1

  • Number of Pages: XIII, 151

  • Number of Illustrations: 233 b/w illustrations, 24 illustrations in colour

  • Topics: Organic Chemistry, Catalysis, Theoretical and Computational Chemistry

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