{"id":{"repo_id":"colostate","oai_identifier":"oai:mountainscholar.org:10217/235839"},"canonical_url":"https://search.dev.ndltd.org/etd/colostate/oai:mountainscholar.org:10217/235839","repository":{"repo_id":"colostate","name":"Colorado State University","base_url":"https://api.mountainscholar.org/server/oai/request"},"display":{"title":"The asymmetric synthesis of amino acids via electrophilic glycinates","abstract":"A new asymmetric synthesis of α-monosubstituted-α-amino acids using D- and L-erythro-4-benzy loxycarbonyl-5,6-diphenyl-2,3,5,6-tetrahydro-1,4-oxazin-2-ones 108 as amino acid templates is described. Bromination of 108 with NBS generates the key electrophilic glycinate 132 which couples with a variety of carbon nucleophiles with high diastereoselectivity to afford the amino acid precursors 134. Catalytic hydrogenation of homologated heterocycles 134 directly furnishes the zwitterionic α-amino acids in high enantiomeric excess. Dissolving metal reduction of 134 permits the preparation of unsaturated amino acids while use of erythro-4-t-butoxycarbonyl-5,6-diphenyl-2,3,5,6-tetrahydro-1,4-oxazin-2-one 160 allows the direct preparation of t-BOC protected α-amino acids. The synthetic approaches to a number of biologically interesting amino acids are described and mechanistic aspects of the coupling reaction are discussed.","abstract_html":"A new asymmetric synthesis of α-monosubstituted-α-amino acids using D- and L-erythro-4-benzy loxycarbonyl-5,6-diphenyl-2,3,5,6-tetrahydro-1,4-oxazin-2-ones 108 as amino acid templates is described. Bromination of 108 with NBS generates the key electrophilic glycinate 132 which couples with a variety of carbon nucleophiles with high diastereoselectivity to afford the amino acid precursors 134. Catalytic hydrogenation of homologated heterocycles 134 directly furnishes the zwitterionic α-amino acids in high enantiomeric excess. Dissolving metal reduction of 134 permits the preparation of unsaturated amino acids while use of erythro-4-t-butoxycarbonyl-5,6-diphenyl-2,3,5,6-tetrahydro-1,4-oxazin-2-one 160 allows the direct preparation of t-BOC protected α-amino acids. The synthetic approaches to a number of biologically interesting amino acids are described and mechanistic aspects of the coupling reaction are discussed.","abstract_has_math":false,"creators":["Sinclair, Peter John, author","Williams, Robert M., advisor"],"institution":"Colorado State University. Libraries","degree_name":"Doctor of Philosophy (Ph.D.)","degree_level":"Doctoral","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":1987,"date_issued":"1987","date_published":"1987","updated_at":"2026-07-27T19:13:18Z","subjects":["Amino acids -- Synthesis"],"languages":["eng","English"],"rights":["Copyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright."],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://doi.org/10.25675/3.024707"],"render_values":[{"text":"https://doi.org/10.25675/3.024707","href":"https://doi.org/10.25675/3.024707","code":true}]}]},"links":{"outbound_url":"https://hdl.handle.net/10217/235839","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Sinclair, Peter John, author","Williams, Robert M., advisor"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2022-11-28T17:44:52Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2022-11-28T17:44:52Z"]},{"key":"dc:date.issued","label":"Date","values":["1987"]},{"key":"dc:publisher","label":"Institution","values":["Colorado State University. 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Catalytic hydrogenation of homologated heterocycles 134 directly furnishes the zwitterionic α-amino acids in high enantiomeric excess. Dissolving metal reduction of 134 permits the preparation of unsaturated amino acids while use of erythro-4-t-butoxycarbonyl-5,6-diphenyl-2,3,5,6-tetrahydro-1,4-oxazin-2-one 160 allows the direct preparation of t-BOC protected α-amino acids. The synthetic approaches to a number of biologically interesting amino acids are described and mechanistic aspects of the coupling reaction are discussed."]},{"key":"dc:format.medium","label":"Dc Format Medium","values":["doctoral dissertations"]},{"key":"dc:title","label":"Title","values":["The asymmetric synthesis of amino acids via electrophilic glycinates"]}]}],"canonical_facts":{"dc:creator":["Sinclair, Peter John, author","Williams, Robert M., advisor"],"dc:date.accessioned":["2022-11-28T17:44:52Z"],"dc:date.available":["2022-11-28T17:44:52Z"],"dc:date.issued":["1987"],"dc:description.abstract":["A new asymmetric synthesis of α-monosubstituted-α-amino acids using D- and L-erythro-4-benzy loxycarbonyl-5,6-diphenyl-2,3,5,6-tetrahydro-1,4-oxazin-2-ones 108 as amino acid templates is described. Bromination of 108 with NBS generates the key electrophilic glycinate 132 which couples with a variety of carbon nucleophiles with high diastereoselectivity to afford the amino acid precursors 134. Catalytic hydrogenation of homologated heterocycles 134 directly furnishes the zwitterionic α-amino acids in high enantiomeric excess. Dissolving metal reduction of 134 permits the preparation of unsaturated amino acids while use of erythro-4-t-butoxycarbonyl-5,6-diphenyl-2,3,5,6-tetrahydro-1,4-oxazin-2-one 160 allows the direct preparation of t-BOC protected α-amino acids. The synthetic approaches to a number of biologically interesting amino acids are described and mechanistic aspects of the coupling reaction are discussed."],"dc:format.medium":["doctoral dissertations"],"dc:identifier.uri":["https://hdl.handle.net/10217/235839","https://doi.org/10.25675/3.024707"],"dc:language":["English"],"dc:language.iso":["eng"],"dc:publisher":["Colorado State University. 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