{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/116139"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/116139","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Synthesis and troubleshooting of chiral 1,2-amino alcohols leading to highly substituted bisoxazoline ligands","abstract":"Submission original under an indefinite embargo labeled 'Open Access'. The submission was exported from vireo on 2022-11-15 without embargo terms","abstract_html":"Submission original under an indefinite embargo labeled 'Open Access'. The submission was exported from vireo on 2022-11-15 without embargo terms","abstract_has_math":false,"creators":["Kwong, Adon Calvin"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"M.S.","degree_level":"Thesis","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Denmark, Scott E"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2022,"date_issued":"2022-08","date_published":"2022-08","updated_at":"2026-07-22T22:24:55Z","subjects":["Bisoxazoline","Ligand","1","2-Amino Alcohols","Chemoinformatics"],"languages":["en","eng"],"rights":["Copyright 2022 Adon Kwong"],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://hdl.handle.net/2142/116139","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Denmark, Scott E"]},{"key":"dc:creator","label":"Author","values":["Kwong, Adon Calvin"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2022-08","2022-05-17"]},{"key":"dc:type","label":"Dc Type","values":["text","Thesis"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["M.S."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Bisoxazoline","Ligand","1","2-Amino Alcohols","Chemoinformatics"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["en","eng"]},{"key":"dc:rights","label":"Dc Rights","values":["Copyright 2022 Adon Kwong"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://hdl.handle.net/2142/116139"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Submission original under an indefinite embargo labeled 'Open Access'. The submission was exported from vireo on 2022-11-15 without embargo terms","The student, Adon Kwong, accepted the attached license on 2022-05-05 at 14:45.","The student, Adon Kwong, submitted this Thesis for approval on 2022-05-05 at 15:10.","This Thesis was approved for publication on 2022-05-17 at 13:52.","DSpace SAF Submission Ingestion Package generated from Vireo submission #18019 on 2022-11-15 at 17:37:24","In asymmetric reaction development, catalyst design has generally been driven by empirical optimization. Chemoinformatics can provide an attractive alternative by predicting selective catalysts with trained machine learning algorithms. Our group is currently developing algorithms to generate descriptors that quantify steric and electronic properties for thousands of candidate molecules. Synthesizing and evaluating stereoselective ligands is crucial in optimizing the algorithm and producing more refined predictions. Chapter 1 discusses the background of 2,2’-(methylene)bisoxazoline (BOX) ligands in the context of chemoinformatics. Within the chemoinformatic workflow, generation of a large in silico library of synthetically accessible ligands with structural diversity is required. The BOX ligand was identified as a desirable ligand class because its highly modular and diversifiable scaffold. To synthesize representatives to generate data for machine-learning modeling, a general, asymmetric synthesis of novel 4,5-polysubstituted bisoxazoline ligands was devised. Chapter 2 discusses the development of novel unified strategy for the asymmetric synthesis of highly substituted BOX ligands. Exploration of the method to construct chiral 1,2-amino alcohols through addition of aryl lithium reagents to Ellman sulfinimines, followed by construction of the BOX ligands, is discussed. Chapter 3 discusses troubleshooting and optimization of key steps in the synthesis of a brief selection of low-yielding bisoxazoline ligands. Certain BOX ligands required for other chemoinformatics projects were problematic to synthesize due to several low-yielding steps, making it implausible to furnish enough to generate data in machine-learning modeling. Individual optimization is attempted to achieve gram-scale synthesis for target bisoxazolines."]},{"key":"dc:format","label":"Dc Format","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Synthesis and troubleshooting of chiral 1,2-amino alcohols leading to highly substituted bisoxazoline ligands"]}]}],"canonical_facts":{"dc:contributor":["Denmark, Scott E"],"dc:creator":["Kwong, Adon Calvin"],"dc:date":["2022-08","2022-05-17"],"dc:description":["Submission original under an indefinite embargo labeled 'Open Access'. The submission was exported from vireo on 2022-11-15 without embargo terms","The student, Adon Kwong, accepted the attached license on 2022-05-05 at 14:45.","The student, Adon Kwong, submitted this Thesis for approval on 2022-05-05 at 15:10.","This Thesis was approved for publication on 2022-05-17 at 13:52.","DSpace SAF Submission Ingestion Package generated from Vireo submission #18019 on 2022-11-15 at 17:37:24","In asymmetric reaction development, catalyst design has generally been driven by empirical optimization. Chemoinformatics can provide an attractive alternative by predicting selective catalysts with trained machine learning algorithms. Our group is currently developing algorithms to generate descriptors that quantify steric and electronic properties for thousands of candidate molecules. Synthesizing and evaluating stereoselective ligands is crucial in optimizing the algorithm and producing more refined predictions. Chapter 1 discusses the background of 2,2’-(methylene)bisoxazoline (BOX) ligands in the context of chemoinformatics. Within the chemoinformatic workflow, generation of a large in silico library of synthetically accessible ligands with structural diversity is required. The BOX ligand was identified as a desirable ligand class because its highly modular and diversifiable scaffold. To synthesize representatives to generate data for machine-learning modeling, a general, asymmetric synthesis of novel 4,5-polysubstituted bisoxazoline ligands was devised. Chapter 2 discusses the development of novel unified strategy for the asymmetric synthesis of highly substituted BOX ligands. Exploration of the method to construct chiral 1,2-amino alcohols through addition of aryl lithium reagents to Ellman sulfinimines, followed by construction of the BOX ligands, is discussed. Chapter 3 discusses troubleshooting and optimization of key steps in the synthesis of a brief selection of low-yielding bisoxazoline ligands. Certain BOX ligands required for other chemoinformatics projects were problematic to synthesize due to several low-yielding steps, making it implausible to furnish enough to generate data in machine-learning modeling. Individual optimization is attempted to achieve gram-scale synthesis for target bisoxazolines."],"dc:format":["application/pdf"],"dc:identifier":["https://hdl.handle.net/2142/116139"],"dc:language":["en","eng"],"dc:rights":["Copyright 2022 Adon Kwong"],"dc:subject":["Bisoxazoline","Ligand","1","2-Amino Alcohols","Chemoinformatics"],"dc:title":["Synthesis and troubleshooting of chiral 1,2-amino alcohols leading to highly substituted bisoxazoline ligands"],"dc:type":["text","Thesis"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Thesis"],"thesis:degree_name":["M.S."],"thesis:institution_name":["University of Illinois at Urbana-Champaign"]},"updated_at":"2026-07-22T22:24:55Z"}