Date of Award

2014

Document type

Thesis

Degree Name

PhD (Doctor of Philosophy)

First Supervisor

Professor Mauro Adamo

Keywords

Chemistry, Pharmaceutical, Organic, Catalysis

Abstract

“For full abstract, see theses”

The development of novel asymmetric reactions enhances both the variety of compounds available and the efficiency with which they can be produced. Chiral compound are hugely important in pharmaceuticals due to the chiral nature of biology. Herein, we describe the use of asymmetric organocatalysts in a Kemp elimination to produce chiral nitriles and fluoronitriles (Scheme I).

Scheme I Asymmetric Kemp elimination. (Diagram)

Scheme I Asymmetric Kemp elimination. We develop an enantioselective procedure for the synthesis of 3-ketosulfonates and the sulfonate directed reduction to 3-hydroxysulfonates. Further development o f this chemistry has lead to a variety o f sulfonate derivatives which could be used in chiral resolution as well as asymmetric organic synthesis (Scheme II).

Scheme II Asymmetric sulfonate derivatives. (Diagram)



Creative Commons License

Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 4.0 License.

File Size

10.3 MB

Comments

A thesis submitted for the degree of Doctor of Philosophy from the Royal College of Surgeons in Ireland in 2014.

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