{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/101375"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/101375","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Allylic C—H activation to access anti-1,3-amino alcohol motifs","abstract":"1,3-Amino alcohols are common motifs in a variety of biologically active molecules including antivirals, antibiotics, antifungals, and various alkaloids. Due to their prevalence and utility as synthetic intermediates, a variety of methods have been developed to access these motifs in a diastereoselective fashion, which are outlined in detail herein. This thesis documents a novel approach to access anti-1,3-amino alcohols through an intramolecular palladium (II)/sulfoxide-oxazoline catalyzed C—H functionalization between a terminal olefin and an N-tosyl carbamate, generating anti-1,3-oxazinanones. These motifs can be further elaborated upon, making this method ideal for the late stage diversification of complex molecules and pharmaceuticals. This new method can be carried out in the presence of reactive functionality that is not well tolerated by existing methods.","abstract_html":"1,3-Amino alcohols are common motifs in a variety of biologically active molecules including antivirals, antibiotics, antifungals, and various alkaloids. Due to their prevalence and utility as synthetic intermediates, a variety of methods have been developed to access these motifs in a diastereoselective fashion, which are outlined in detail herein. This thesis documents a novel approach to access anti-1,3-amino alcohols through an intramolecular palladium (II)/sulfoxide-oxazoline catalyzed C—H functionalization between a terminal olefin and an N-tosyl carbamate, generating anti-1,3-oxazinanones. These motifs can be further elaborated upon, making this method ideal for the late stage diversification of complex molecules and pharmaceuticals. This new method can be carried out in the presence of reactive functionality that is not well tolerated by existing methods.","abstract_has_math":false,"creators":["Young, Jonathon Michael"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"M.S.","degree_level":"Thesis","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["White, Maria C."],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2018,"date_issued":"2018-09-04T20:47:30Z","date_published":"2018-09-04T20:47:30Z","updated_at":"2026-07-22T22:24:40Z","subjects":["C—H activation, organometallics"],"languages":["en"],"rights":["Copyright 2018 Jonathon Young"],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/2142/101375","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["White, Maria C."]},{"key":"dc:creator","label":"Author","values":["Young, Jonathon Michael"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2018-09-04T20:47:30Z","2020-09-05T09:15:26Z","2018-04-25","2018-05"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"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":["C—H activation, organometallics"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["en"]},{"key":"dc:rights","label":"Dc Rights","values":["Copyright 2018 Jonathon Young"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/101375"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["1,3-Amino alcohols are common motifs in a variety of biologically active molecules including antivirals, antibiotics, antifungals, and various alkaloids. Due to their prevalence and utility as synthetic intermediates, a variety of methods have been developed to access these motifs in a diastereoselective fashion, which are outlined in detail herein. This thesis documents a novel approach to access anti-1,3-amino alcohols through an intramolecular palladium (II)/sulfoxide-oxazoline catalyzed C—H functionalization between a terminal olefin and an N-tosyl carbamate, generating anti-1,3-oxazinanones. These motifs can be further elaborated upon, making this method ideal for the late stage diversification of complex molecules and pharmaceuticals. This new method can be carried out in the presence of reactive functionality that is not well tolerated by existing methods.","Submission published under a 24 month embargo labeled 'Closed Access', the embargo will last until 2020-05-01","The student, Jonathon Young, accepted the attached license on 2018-04-25 at 09:29.","The student, Jonathon Young, submitted this Thesis for approval on 2018-04-25 at 09:40.","This Thesis was approved for publication on 2018-04-25 at 14:08.","DSpace SAF Submission Ingestion Package generated from Vireo submission #12470 on 2018-08-31 at 17:30:26","Made available in DSpace on 2018-09-04T20:47:30Z (GMT). No. of bitstreams: 2 YOUNG-THESIS-2018.pdf: 17381393 bytes, checksum: e7e97dc99ab1ce290a64d3a5a9836002 (MD5) LICENSE.txt: 4211 bytes, checksum: 6e0b64d3ab5cba30177cd6924932d927 (MD5) Previous issue date: 2018-04-25","Embargo set by: Seth Robbins for item 107460 Lift date: 2020-09-04T20:47:38Z Reason: Author requested closed access (OA after 2yrs) in Vireo ETD system","Embargo set by: Seth Robbins for item 107460 Lift date: 2020-09-04T20:50:11Z Reason: Author requested closed access (OA after 2yrs) in Vireo ETD system","Limited Restriction Lifted for Item 107460 on 2020-09-05T09:15:26Z."]},{"key":"dc:format","label":"Dc Format","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Allylic C—H activation to access anti-1,3-amino alcohol motifs"]}]}],"canonical_facts":{"dc:contributor":["White, Maria C."],"dc:creator":["Young, Jonathon Michael"],"dc:date":["2018-09-04T20:47:30Z","2020-09-05T09:15:26Z","2018-04-25","2018-05"],"dc:description":["1,3-Amino alcohols are common motifs in a variety of biologically active molecules including antivirals, antibiotics, antifungals, and various alkaloids. Due to their prevalence and utility as synthetic intermediates, a variety of methods have been developed to access these motifs in a diastereoselective fashion, which are outlined in detail herein. This thesis documents a novel approach to access anti-1,3-amino alcohols through an intramolecular palladium (II)/sulfoxide-oxazoline catalyzed C—H functionalization between a terminal olefin and an N-tosyl carbamate, generating anti-1,3-oxazinanones. These motifs can be further elaborated upon, making this method ideal for the late stage diversification of complex molecules and pharmaceuticals. This new method can be carried out in the presence of reactive functionality that is not well tolerated by existing methods.","Submission published under a 24 month embargo labeled 'Closed Access', the embargo will last until 2020-05-01","The student, Jonathon Young, accepted the attached license on 2018-04-25 at 09:29.","The student, Jonathon Young, submitted this Thesis for approval on 2018-04-25 at 09:40.","This Thesis was approved for publication on 2018-04-25 at 14:08.","DSpace SAF Submission Ingestion Package generated from Vireo submission #12470 on 2018-08-31 at 17:30:26","Made available in DSpace on 2018-09-04T20:47:30Z (GMT). No. of bitstreams: 2 YOUNG-THESIS-2018.pdf: 17381393 bytes, checksum: e7e97dc99ab1ce290a64d3a5a9836002 (MD5) LICENSE.txt: 4211 bytes, checksum: 6e0b64d3ab5cba30177cd6924932d927 (MD5) Previous issue date: 2018-04-25","Embargo set by: Seth Robbins for item 107460 Lift date: 2020-09-04T20:47:38Z Reason: Author requested closed access (OA after 2yrs) in Vireo ETD system","Embargo set by: Seth Robbins for item 107460 Lift date: 2020-09-04T20:50:11Z Reason: Author requested closed access (OA after 2yrs) in Vireo ETD system","Limited Restriction Lifted for Item 107460 on 2020-09-05T09:15:26Z."],"dc:format":["application/pdf"],"dc:identifier":["http://hdl.handle.net/2142/101375"],"dc:language":["en"],"dc:rights":["Copyright 2018 Jonathon Young"],"dc:subject":["C—H activation, organometallics"],"dc:title":["Allylic C—H activation to access anti-1,3-amino alcohol motifs"],"dc:type":["text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Thesis"],"thesis:degree_name":["M.S."],"thesis:institution_name":["University of Illinois at Urbana-Champaign"]},"updated_at":"2026-07-22T22:24:40Z"}