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Enantioselective Preparation of Bromides and its Application to the Preparation of Bioactive Compounds

thesis
posted on 11.03.2022, 15:03 authored by Caterina CioffiCaterina Cioffi

The aim of this project is based on the optimization of new route of synthesis of phenyl alkyl halides, in particular benzylic bromides that are considered versatile intermediates in organic synthesis and often employed in the preparation of bioactive materials. Though this project, we have provided an innovative method that is alternative to methodologies based on phosphorous (III) and (V) for the preparation of bromides having EWG group in β position. This procedure allowed to by-pass the methodologies based on the oxygen-based leaving group and their significant drawnbacks, such as bromide product racemisation and undesired alkene side product arising from elimination of sensitive bromides. Moreover, we have showed that the oxidative activation of sulphide via SN2 could be useful for the development of C-X bond forming reactions. We showed how alkyl bromides and chlorides could be employed for the preparation of Carbon-Oxygen bond in bioactive molecules such as API with an aryl propanamine core. For example, a full synthesis of five steps is showed for the synthesis of Atomoxetine, anti-depressant known as Strattera.

Funding

EPSPG2016185

History

First Supervisor

Prof. Mauro F. A. Adamo

Comments

Submitted for the Award of Doctor of Philosophy to the Royal College of Surgeons in Ireland, 2021.

Published Citation

Cioffi C. Enantioselective Preparation of Bromides and its Application to the Preparation of Bioactive Compounds [PhD Thesis] Dublin: Royal College of Surgeons in Ireland; 2021

Degree Name

Doctor of Philosophy (PhD)

Date of award

31/05/2021

Programme

  • Doctor of Philosophy (PhD)

Research Area

  • Chemistry and Pharmaceutical Sciences

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