{"id":{"repo_id":"glasgow","oai_identifier":"oai:theses.gla.ac.uk:532"},"canonical_url":"https://search.dev.ndltd.org/etd/glasgow/oai:theses.gla.ac.uk:532","repository":{"repo_id":"glasgow","name":"University of Glasgow","base_url":"https://theses.gla.ac.uk/cgi/oai2"},"display":{"title":"Synthesis and application of pinene-pyridine derivatives in asymmetric catalysis","abstract":"The research described herein focuses on the synthesis of chiral pinene-pyridine derivatives, and their application in asymmetric catalysis. Both transition metal catalysed and organocatalytic transformations were investigated. Chiral pyridine-phosphines based on α-pinene were synthesised and applied as efficient P,N-ligands for the enantioselective palladium(II)-catalysed Baeyer-Villiger oxidation of prochiral 3-substituted cyclobutanones to furnish chiral γ-butyrolactones in up to 81% ee. Complexes of these ligands with iridium can also promote asymmetric hydrogenation of olefins in up to 83% ee. Novel N,N’-dioxides were synthesised from α-pinene and a range of 2-pyridine-acetophenones by employing Kröhnke annulation reaction as the key cyclisation step. Although poor enantioselectivity was achieved (up to 12% ee), high reactivity of the catalysts is, however, promising.","abstract_html":"The research described herein focuses on the synthesis of chiral pinene-pyridine derivatives, and their application in asymmetric catalysis. Both transition metal catalysed and organocatalytic transformations were investigated. Chiral pyridine-phosphines based on α-pinene were synthesised and applied as efficient P,N-ligands for the enantioselective palladium(II)-catalysed Baeyer-Villiger oxidation of prochiral 3-substituted cyclobutanones to furnish chiral γ-butyrolactones in up to 81% ee. Complexes of these ligands with iridium can also promote asymmetric hydrogenation of olefins in up to 83% ee. Novel N,N’-dioxides were synthesised from α-pinene and a range of 2-pyridine-acetophenones by employing Kröhnke annulation reaction as the key cyclisation step. Although poor enantioselectivity was achieved (up to 12% ee), high reactivity of the catalysts is, however, promising.","abstract_has_math":false,"creators":["Friscourt, Frederic"],"institution":"University of Glasgow","degree_name":null,"degree_level":"PhD","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2008,"date_issued":"2008","date_published":"2008","updated_at":"2026-07-24T02:23:26Z","subjects":["QD Chemistry"],"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":["Friscourt, Frederic"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2008"]},{"key":"dc:date.issued","label":"Date","values":["2008"]},{"key":"dc:publisher.institution","label":"Dc Publisher Institution","values":["University of Glasgow"]},{"key":"dc:relation.isreferencedby","label":"Dc Relation Isreferencedby","values":["https://theses.gla.ac.uk/532/"]},{"key":"dc:relation.isreferencedby.uri","label":"Dc Relation Isreferencedby URI","values":["https://gla.on.worldcat.org/oclc/1547480927"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"dc:type.qualificationlevel","label":"Dc Type Qualificationlevel","values":["PhD"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["QD Chemistry"]}]},{"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://theses.gla.ac.uk/532/1/2008friscourt1phd.pdf"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The research described herein focuses on the synthesis of chiral pinene-pyridine derivatives, and their application in asymmetric catalysis. Both transition metal catalysed and organocatalytic transformations were investigated. Chiral pyridine-phosphines based on α-pinene were synthesised and applied as efficient P,N-ligands for the enantioselective palladium(II)-catalysed Baeyer-Villiger oxidation of prochiral 3-substituted cyclobutanones to furnish chiral γ-butyrolactones in up to 81% ee. Complexes of these ligands with iridium can also promote asymmetric hydrogenation of olefins in up to 83% ee. Novel N,N’-dioxides were synthesised from α-pinene and a range of 2-pyridine-acetophenones by employing Kröhnke annulation reaction as the key cyclisation step. Although poor enantioselectivity was achieved (up to 12% ee), high reactivity of the catalysts is, however, promising."]},{"key":"dc:format","label":"Dc Format","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Synthesis and application of pinene-pyridine derivatives in asymmetric catalysis"]}]}],"canonical_facts":{"dc:creator":["Friscourt, Frederic"],"dc:date":["2008"],"dc:date.issued":["2008"],"dc:description.abstract":["The research described herein focuses on the synthesis of chiral pinene-pyridine derivatives, and their application in asymmetric catalysis. Both transition metal catalysed and organocatalytic transformations were investigated. Chiral pyridine-phosphines based on α-pinene were synthesised and applied as efficient P,N-ligands for the enantioselective palladium(II)-catalysed Baeyer-Villiger oxidation of prochiral 3-substituted cyclobutanones to furnish chiral γ-butyrolactones in up to 81% ee. Complexes of these ligands with iridium can also promote asymmetric hydrogenation of olefins in up to 83% ee. Novel N,N’-dioxides were synthesised from α-pinene and a range of 2-pyridine-acetophenones by employing Kröhnke annulation reaction as the key cyclisation step. Although poor enantioselectivity was achieved (up to 12% ee), high reactivity of the catalysts is, however, promising."],"dc:format":["application/pdf"],"dc:identifier.uri":["https://theses.gla.ac.uk/532/1/2008friscourt1phd.pdf"],"dc:language":["en"],"dc:publisher.institution":["University of Glasgow"],"dc:relation.isreferencedby":["https://theses.gla.ac.uk/532/"],"dc:relation.isreferencedby.uri":["https://gla.on.worldcat.org/oclc/1547480927"],"dc:subject":["QD Chemistry"],"dc:title":["Synthesis and application of pinene-pyridine derivatives in asymmetric catalysis"],"dc:type":["Thesis"],"dc:type.qualificationlevel":["PhD"]},"updated_at":"2026-07-24T02:23:26Z"}