{"id":{"repo_id":"houston","oai_identifier":"oai:uh-ir.tdl.org:10657/2870"},"canonical_url":"https://search.dev.ndltd.org/etd/houston/oai:uh-ir.tdl.org:10657/2870","repository":{"repo_id":"houston","name":"University of Houston","base_url":"https://uh-ir.tdl.org/server/oai/request"},"display":{"title":"Asymmetric α-Alkylation of Acyclic Ketones Utilizing Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones","abstract":"Asymmetric variants of ketone α-alkylation are highly important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketone or derivatives thereof. A method for asymmetric α-alkylation of ketones using N-Amino cyclic carbamate (ACC) chiral auxiliaries is described. ACC alkylation delivers excellent stereoselectivity and yields, with a camphor-derived ACC auxiliary exhibits the highest stereoselectivities. A full account of this ACC method is discussed herein, including the synthesis of camphor-derived ACC auxiliaries, an amination method for preparation of ACC auxiliaries from commercially available oxazolidinones, and the study of the regioselectivity and diastereoselectivity of ACC hydrazone alkylation to determine factors compromising the selectivities.","abstract_html":"Asymmetric variants of ketone α-alkylation are highly important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketone or derivatives thereof. A method for asymmetric α-alkylation of ketones using N-Amino cyclic carbamate (ACC) chiral auxiliaries is described. ACC alkylation delivers excellent stereoselectivity and yields, with a camphor-derived ACC auxiliary exhibits the highest stereoselectivities. A full account of this ACC method is discussed herein, including the synthesis of camphor-derived ACC auxiliaries, an amination method for preparation of ACC auxiliaries from commercially available oxazolidinones, and the study of the regioselectivity and diastereoselectivity of ACC hydrazone alkylation to determine factors compromising the selectivities.","abstract_has_math":false,"creators":["Huynh, Uyen 1986-"],"institution":"University of Houston","degree_name":"Doctor of Philosophy","degree_level":"Doctoral","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":["Coltart, Don M."],"committee_chairs":[],"committee_members":["May, Jeremy A.","Miljanić, Ognjen Š.","Teets, Thomas S.","Bornmann, William G."],"year":2017,"date_issued":"2017-12","date_published":"2017-12","updated_at":"2026-07-24T02:32:47Z","subjects":["ACC auxiliary","Ketone alpha alkylation","Azaenolate","Enantioselective","Asymmetric","Carbon–carbon bond formation","Amination","Monochloramine"],"languages":["eng"],"rights":["The author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s)."],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/10657/2870","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Coltart, Don M."]},{"key":"dc:contributor.committeemember","label":"Committee Member","values":["May, Jeremy A.","Miljanić, Ognjen Š.","Teets, Thomas S.","Bornmann, William G."]},{"key":"dc:creator","label":"Author","values":["Huynh, Uyen 1986-"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2018-03-12T18:31:00Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2018-03-12T18:31:00Z"]},{"key":"dc:date.issued","label":"Date","values":["2017-12"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Doctoral"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Doctor of Philosophy"]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Houston"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["ACC auxiliary","Ketone alpha alkylation","Azaenolate","Enantioselective","Asymmetric","Carbon–carbon bond formation","Amination","Monochloramine"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["eng"]},{"key":"dc:rights","label":"Dc Rights","values":["The author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s)."]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["http://hdl.handle.net/10657/2870"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Asymmetric variants of ketone α-alkylation are highly important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketone or derivatives thereof. A method for asymmetric α-alkylation of ketones using N-Amino cyclic carbamate (ACC) chiral auxiliaries is described. ACC alkylation delivers excellent stereoselectivity and yields, with a camphor-derived ACC auxiliary exhibits the highest stereoselectivities. A full account of this ACC method is discussed herein, including the synthesis of camphor-derived ACC auxiliaries, an amination method for preparation of ACC auxiliaries from commercially available oxazolidinones, and the study of the regioselectivity and diastereoselectivity of ACC hydrazone alkylation to determine factors compromising the selectivities."]},{"key":"dc:format.mimetype","label":"Dc Format Mimetype","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Asymmetric α-Alkylation of Acyclic Ketones Utilizing Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones"]}]}],"canonical_facts":{"dc:contributor.advisor":["Coltart, Don M."],"dc:contributor.committeemember":["May, Jeremy A.","Miljanić, Ognjen Š.","Teets, Thomas S.","Bornmann, William G."],"dc:creator":["Huynh, Uyen 1986-"],"dc:date.accessioned":["2018-03-12T18:31:00Z"],"dc:date.available":["2018-03-12T18:31:00Z"],"dc:date.issued":["2017-12"],"dc:description.abstract":["Asymmetric variants of ketone α-alkylation are highly important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketone or derivatives thereof. A method for asymmetric α-alkylation of ketones using N-Amino cyclic carbamate (ACC) chiral auxiliaries is described. ACC alkylation delivers excellent stereoselectivity and yields, with a camphor-derived ACC auxiliary exhibits the highest stereoselectivities. A full account of this ACC method is discussed herein, including the synthesis of camphor-derived ACC auxiliaries, an amination method for preparation of ACC auxiliaries from commercially available oxazolidinones, and the study of the regioselectivity and diastereoselectivity of ACC hydrazone alkylation to determine factors compromising the selectivities."],"dc:format.mimetype":["application/pdf"],"dc:identifier.uri":["http://hdl.handle.net/10657/2870"],"dc:language.iso":["eng"],"dc:rights":["The author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s)."],"dc:subject":["ACC auxiliary","Ketone alpha alkylation","Azaenolate","Enantioselective","Asymmetric","Carbon–carbon bond formation","Amination","Monochloramine"],"dc:title":["Asymmetric α-Alkylation of Acyclic Ketones Utilizing Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Doctoral"],"thesis:degree_name":["Doctor of Philosophy"],"thesis:institution_name":["University of Houston"]},"updated_at":"2026-07-24T02:32:47Z"}