{"id":{"repo_id":"east-anglia","oai_identifier":"oai:ueaeprints.uea.ac.uk:42423"},"canonical_url":"https://search.dev.ndltd.org/etd/east-anglia/oai:ueaeprints.uea.ac.uk:42423","repository":{"repo_id":"east-anglia","name":"University of East Anglia","base_url":"https://ueaeprints.uea.ac.uk/cgi/oai2"},"display":{"title":"Studies towards the Organocatalytic ‘Dialled In’ Synthesis of Chiral, Non-Racemic Aziridines, and Amino Acids, Containing Multiple Isotopic Labels","abstract":"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.","abstract_html":"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.","abstract_has_math":false,"creators":["Thurston, Sean"],"institution":"University of East Anglia","degree_name":"phd","degree_level":"doctoral","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2012,"date_issued":"2012-10","date_published":"2012-10","updated_at":"2026-07-24T02:11:54Z","subjects":[],"languages":["en"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":null,"outbound_label":null,"outbound_source":null},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Thurston, Sean"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2012-10"]},{"key":"dc:date.issued","label":"Date","values":["2012-10"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["School of Chemistry"]},{"key":"dc:publisher.institution","label":"Dc Publisher Institution","values":["University of East Anglia"]},{"key":"dc:relation.isreferencedby","label":"Dc Relation Isreferencedby","values":["https://ueaeprints.uea.ac.uk/id/eprint/42423/"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"dc:type.qualificationlevel","label":"Dc Type Qualificationlevel","values":["doctoral"]},{"key":"dc:type.qualificationname","label":"Dc Type Qualificationname","values":["phd"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["en"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://ueaeprints.uea.ac.uk/id/eprint/42423/1/2012ThurstonSTPhD.pdf"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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."]},{"key":"dc:format","label":"Dc Format","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Studies towards the Organocatalytic ‘Dialled In’ Synthesis of Chiral, Non-Racemic Aziridines, and Amino Acids, Containing Multiple Isotopic Labels"]}]}],"canonical_facts":{"dc:creator":["Thurston, Sean"],"dc:date":["2012-10"],"dc:date.issued":["2012-10"],"dc:description.abstract":["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."],"dc:format":["application/pdf"],"dc:identifier.uri":["https://ueaeprints.uea.ac.uk/id/eprint/42423/1/2012ThurstonSTPhD.pdf"],"dc:language":["en"],"dc:publisher.department":["School of Chemistry"],"dc:publisher.institution":["University of East Anglia"],"dc:relation.isreferencedby":["https://ueaeprints.uea.ac.uk/id/eprint/42423/"],"dc:title":["Studies towards the Organocatalytic ‘Dialled In’ Synthesis of Chiral, Non-Racemic Aziridines, and Amino Acids, Containing Multiple Isotopic Labels"],"dc:type":["Thesis"],"dc:type.qualificationlevel":["doctoral"],"dc:type.qualificationname":["phd"]},"updated_at":"2026-07-24T02:11:54Z"}