{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/84433"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/84433","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Enantioselective Alpha-Lithiation of N-Boc-N-(p-Methoxyphenyl)allylamines Mediated by (--)-Sparteine","abstract":"Tin-lithium exchange of enantioenriched allylic stannanes in the presence of (-)-sparteine followed by electrophilic substitution provides enecarbamates with configurations opposite to that obtained by the deprotonation sequence. The enecarbamates can be hydrolyzed to aldehydes or reduced to amines, and therefore provide facile entry into chiral homoenolate synthetic equivalents and chiral gamma-lithioamine synthetic equivalents.","abstract_html":"Tin-lithium exchange of enantioenriched allylic stannanes in the presence of (-)-sparteine followed by electrophilic substitution provides enecarbamates with configurations opposite to that obtained by the deprotonation sequence. The enecarbamates can be hydrolyzed to aldehydes or reduced to amines, and therefore provide facile entry into chiral homoenolate synthetic equivalents and chiral gamma-lithioamine synthetic equivalents.","abstract_has_math":false,"creators":["Weisenburger, Gerald Allen"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Beak, Peter"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2015,"date_issued":"2015-09-25T22:14:28Z","date_published":"2015-09-25T22:14:28Z","updated_at":"2026-07-22T22:26:23Z","subjects":["Chemistry, Organic"],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(MiAaPQ)AAI9912426"],"render_values":[{"text":"(MiAaPQ)AAI9912426","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/84433","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Beak, Peter"]},{"key":"dc:creator","label":"Author","values":["Weisenburger, Gerald Allen"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2015-09-25T22:14:28Z","10000-01-01","1998"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"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":["Chemistry, Organic"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/84433","(MiAaPQ)AAI9912426"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Tin-lithium exchange of enantioenriched allylic stannanes in the presence of (-)-sparteine followed by electrophilic substitution provides enecarbamates with configurations opposite to that obtained by the deprotonation sequence. 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