Date of Award
PhD (Doctor of Philosophy)
Professor Mauro Adamo
Chemistry, Pharmaceutical, Organic, Catalysis
“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)
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Duffy CJ. Studies concerning the preparation of enantiopure intermediates for the manufacture of diagnostics. [PhD Thesis]. Dublin: Royal College of Surgeons in Ireland; 2014.