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Title: Studies towards the organocatalytic 'dialled in' synthesis of chiral, non-racemic aziridines, and amino acids, containing multiple isotopic labels
Author: Thurston, Sean
ISNI:       0000 0004 2736 1682
Awarding Body: University of East Anglia
Current Institution: University of East Anglia
Date of Award: 2012
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Within this thesis, a highly effective one-pot methodology (based around the use of the organocatalyst pyridinium triflate) has been developed for the highly cis-selective synthesis of N-aryl 3-aryl-aziridine-2-carboxylates as racemates in yields of up to 80 %. This methodology has been extended by the use of a highly acidic C2 symmetric 3,3’- anthracenyl functionalised BINOL triflylphosphoramide organocatalyst, which allows for the formation of the desired cis- N-aryl 3-aryl-aziridine-2-carboxylates in an effective and highly enantioselective manner (affording the desired materials in yields of up to 81 %, and e.e.s of >99 %). Utilising the methodology developed within the first part of the thesis, enantio- and isotopically enriched cis- N-aryl 3-aryl-aziridine-2-carboxylates have been synthesised in a regioselective manner; with deuterium selectively introduced at the C2, and/or C3 positions of the aziridine ring with generally >90 % isotopic enrichment. Further to this, these aziridines have been submitted to ring opening methodologies in order to produce enantiomerically enriched a-amino acid derivatives bearing regioselectively introduced deuterium labels (with generally >90 % isotopic enrichment), in yields of up to 97 %, and e.e.s of up to 97 %, Finally, these methods have been combined in order to synthesise 5 target molecules consisting of functionalised enantioenriched a-amino acid derivatives bearing multiple isotopic labels including deuterium, 15N, and 18O, in what has become known as the ‘Dialled In’ methodology.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available