{"id":{"repo_id":"windsor","oai_identifier":"oai:uwindsor.scholaris.ca:20.500.14776/2062"},"canonical_url":"https://search.dev.ndltd.org/etd/windsor/oai:uwindsor.scholaris.ca:20.500.14776/2062","repository":{"repo_id":"windsor","name":"University of Windsor","base_url":"https://uwindsor.scholaris.ca/server/oai/request"},"display":{"title":"Induced pi-facial discrimination in the alkylation of chiral derivatives of glycine.","abstract":"Part A. The alkylation trans 2-arylcyclohexyl hippurates with a series of electrophiles was examined. The reaction stereoselectivity varied from 46 to 81% depending on the steric and electronic nature of the electrophile when (Ar = phenyl). Higher stereoselectivity was observed when reacting electrophiles of increasing pi-character. When the chiral auxiliary contained a naphthyl group the stereoselectivity was >80% for every electrophile used. Part B. The alkylation of the trans 2-phenylcyclohexylamide of methyl glycinate with a series of electrophiles was examined. Incorporation of the chiral auxiliary on the amino terminus of the amino acid appears to induce good stereoselectivity only when the electrophiles contain a point of unsaturation. The reaction stereoselectivity ranged from 21 to 80% depending on the electronic nature of the electrophiles. It is proposed that a pi-stacking interaction between the aromatic group on the auxiliary and the unsaturated electrophiles was responsible for the high stereochemical excess observed. Source: Masters Abstracts International, Volume: 39-02, page: 0514. Adviser: John M. McIntosh. Thesis (M.Sc.)--University of Windsor (Canada), 1999.","abstract_html":"Part A. The alkylation trans 2-arylcyclohexyl hippurates with a series of electrophiles was examined. The reaction stereoselectivity varied from 46 to 81% depending on the steric and electronic nature of the electrophile when (Ar = phenyl). Higher stereoselectivity was observed when reacting electrophiles of increasing pi-character. When the chiral auxiliary contained a naphthyl group the stereoselectivity was >80% for every electrophile used. Part B. The alkylation of the trans 2-phenylcyclohexylamide of methyl glycinate with a series of electrophiles was examined. Incorporation of the chiral auxiliary on the amino terminus of the amino acid appears to induce good stereoselectivity only when the electrophiles contain a point of unsaturation. The reaction stereoselectivity ranged from 21 to 80% depending on the electronic nature of the electrophiles. It is proposed that a pi-stacking interaction between the aromatic group on the auxiliary and the unsaturated electrophiles was responsible for the high stereochemical excess observed. Source: Masters Abstracts International, Volume: 39-02, page: 0514. Adviser: John M. McIntosh. Thesis (M.Sc.)--University of Windsor (Canada), 1999.","abstract_has_math":false,"creators":["Peters, Scott Owen."],"institution":"University of Windsor","degree_name":"M.Sc.","degree_level":"Masters","degree_discipline":"Chemistry and Biochemistry","degree_department":null,"school":null,"contributors":[],"advisors":["McIntosh, John M.,"],"committee_chairs":[],"committee_members":[],"year":1999,"date_issued":"1999-01-01","date_published":"1999-01-01","updated_at":"2026-07-27T22:04:52Z","subjects":[],"languages":["en_CA"],"rights":[],"rights_urls":["http://creativecommons.org/licenses/by-nc-nd/4.0/"],"identifier_entries":[]},"links":{"outbound_url":"https://hdl.handle.net/20.500.14776/2062","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["McIntosh, John M.,"]},{"key":"dc:creator","label":"Author","values":["Peters, Scott Owen."]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2025-06-20 10:11"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2013-03-21 8:39","2025-06-20T14:11:18Z"]},{"key":"dc:date.issued","label":"Date","values":["1999-01-01"]},{"key":"dc:type","label":"Dc Type","values":["info:eu-repo/semantics/masterThesis"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry and Biochemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Masters"]},{"key":"thesis:degree_name","label":"Degree Name","values":["M.Sc."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Windsor"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["en_CA"]},{"key":"dc:rights","label":"Dc Rights","values":["http://creativecommons.org/licenses/by-nc-nd/4.0/"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://hdl.handle.net/20.500.14776/2062"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Part A. The alkylation trans 2-arylcyclohexyl hippurates with a series of electrophiles was examined. The reaction stereoselectivity varied from 46 to 81% depending on the steric and electronic nature of the electrophile when (Ar = phenyl). Higher stereoselectivity was observed when reacting electrophiles of increasing pi-character. When the chiral auxiliary contained a naphthyl group the stereoselectivity was >80% for every electrophile used. Part B. The alkylation of the trans 2-phenylcyclohexylamide of methyl glycinate with a series of electrophiles was examined. Incorporation of the chiral auxiliary on the amino terminus of the amino acid appears to induce good stereoselectivity only when the electrophiles contain a point of unsaturation. The reaction stereoselectivity ranged from 21 to 80% depending on the electronic nature of the electrophiles. It is proposed that a pi-stacking interaction between the aromatic group on the auxiliary and the unsaturated electrophiles was responsible for the high stereochemical excess observed. Source: Masters Abstracts International, Volume: 39-02, page: 0514. Adviser: John M. McIntosh. Thesis (M.Sc.)--University of Windsor (Canada), 1999."]},{"key":"dc:title","label":"Title","values":["Induced pi-facial discrimination in the alkylation of chiral derivatives of glycine."]}]}],"canonical_facts":{"dc:contributor.advisor":["McIntosh, John M.,"],"dc:creator":["Peters, Scott Owen."],"dc:date.accessioned":["2025-06-20 10:11"],"dc:date.available":["2013-03-21 8:39","2025-06-20T14:11:18Z"],"dc:date.issued":["1999-01-01"],"dc:description.abstract":["Part A. The alkylation trans 2-arylcyclohexyl hippurates with a series of electrophiles was examined. The reaction stereoselectivity varied from 46 to 81% depending on the steric and electronic nature of the electrophile when (Ar = phenyl). Higher stereoselectivity was observed when reacting electrophiles of increasing pi-character. When the chiral auxiliary contained a naphthyl group the stereoselectivity was >80% for every electrophile used. Part B. The alkylation of the trans 2-phenylcyclohexylamide of methyl glycinate with a series of electrophiles was examined. Incorporation of the chiral auxiliary on the amino terminus of the amino acid appears to induce good stereoselectivity only when the electrophiles contain a point of unsaturation. The reaction stereoselectivity ranged from 21 to 80% depending on the electronic nature of the electrophiles. It is proposed that a pi-stacking interaction between the aromatic group on the auxiliary and the unsaturated electrophiles was responsible for the high stereochemical excess observed. Source: Masters Abstracts International, Volume: 39-02, page: 0514. Adviser: John M. McIntosh. Thesis (M.Sc.)--University of Windsor (Canada), 1999."],"dc:identifier.uri":["https://hdl.handle.net/20.500.14776/2062"],"dc:language.iso":["en_CA"],"dc:rights":["http://creativecommons.org/licenses/by-nc-nd/4.0/"],"dc:title":["Induced pi-facial discrimination in the alkylation of chiral derivatives of glycine."],"dc:type":["info:eu-repo/semantics/masterThesis"],"thesis:degree_discipline":["Chemistry and Biochemistry"],"thesis:degree_level":["Masters"],"thesis:degree_name":["M.Sc."],"thesis:institution_name":["University of Windsor"]},"updated_at":"2026-07-27T22:04:52Z"}