Springer Theses

Selectivity in the Synthesis of Cyclic Sulfonamides

Application in the Synthesis of Natural Products

Authors: Geoghegan, Kimberly

  • 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  • Experimental details provided for all transformations-including unpublished results and procedures
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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.

About the authors

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.

Table of contents (6 chapters)

  • Introduction

    Geoghegan, Kimberly

    Pages 1-15

  • Regioselectivity in the Heck (Mizoroki-Heck) Reaction

    Geoghegan, Kimberly

    Pages 17-41

  • Wagner-Meerwein Rearrangement of Cyclic Sulfonamides

    Geoghegan, Kimberly

    Pages 43-54

  • An Investigation into the One-Pot Heck Olefination-Hydrogenation Reaction

    Geoghegan, Kimberly

    Pages 55-65

  • Double Reduction of Cyclic Aromatic Sulfonamides

    Geoghegan, Kimberly

    Pages 67-79

Buy this book

eBook $99.00
price for USA (gross)
  • ISBN 978-3-319-10338-9
  • Digitally watermarked, DRM-free
  • Included format: EPUB, PDF
  • ebooks can be used on all reading devices
  • Immediate eBook download after purchase
Hardcover $129.00
price for USA
  • ISBN 978-3-319-10337-2
  • Free shipping for individuals worldwide
  • Usually dispatched within 3 to 5 business days.
Softcover $129.00
price for USA
  • ISBN 978-3-319-36431-5
  • Free shipping for individuals worldwide
  • Usually dispatched within 3 to 5 business days.
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Bibliographic Information

Bibliographic Information
Book Title
Selectivity in the Synthesis of Cyclic Sulfonamides
Book Subtitle
Application in the Synthesis of Natural Products
Authors
Series Title
Springer Theses
Copyright
2014
Publisher
Springer International Publishing
Copyright Holder
Springer International Publishing Switzerland
eBook ISBN
978-3-319-10338-9
DOI
10.1007/978-3-319-10338-9
Hardcover ISBN
978-3-319-10337-2
Softcover ISBN
978-3-319-36431-5
Series ISSN
2190-5053
Edition Number
1
Number of Pages
XIII, 151
Number of Illustrations and Tables
233 b/w illustrations, 24 illustrations in colour
Topics