{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/19974"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/19974","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Novel syntheses by directed lithiations of N-Boc benzylamines and cyclopropylamines","abstract":"The lithiation-substitution of N-Boc benzylamines and cyclopropylamines have been investigated to explore the synthetic potential of these substrates. We have achieved the syntheses of highly enantioenriched benzylic $\\alpha$-substituted N-Boc secondary amines using RLi/(-)-sparteine. Extension of this chemistry to asymmetric syntheses of both enantiomers of primary $\\alpha$-substituted benzylamines and $\\alpha,\\alpha$-disubstituted benzylamines has been achieved successfully. Also, the N-Boc group was used as an activating and directing group for the $\\alpha$ and $\\beta$ lithiation-substitution of cyclopropanes. Extension of this chemistry to syntheses of highly functionalized cyclopentane by (3 + 2) cycloaddition and asymmetric synthesis of N-Boc azabicyclic (3.10) hexane was investigated.","abstract_html":"The lithiation-substitution of N-Boc benzylamines and cyclopropylamines have been investigated to explore the synthetic potential of these substrates. We have achieved the syntheses of highly enantioenriched benzylic <span class=\"etd-inline-math\">&alpha;</span>-substituted N-Boc secondary amines using RLi/(-)-sparteine. Extension of this chemistry to asymmetric syntheses of both enantiomers of primary <span class=\"etd-inline-math\">&alpha;</span>-substituted benzylamines and <span class=\"etd-inline-math\">&alpha;,&alpha;</span>-disubstituted benzylamines has been achieved successfully. Also, the N-Boc group was used as an activating and directing group for the <span class=\"etd-inline-math\">&alpha;</span> and <span class=\"etd-inline-math\">&beta;</span> lithiation-substitution of cyclopropanes. Extension of this chemistry to syntheses of highly functionalized cyclopentane by (3 + 2) cycloaddition and asymmetric synthesis of N-Boc azabicyclic (3.10) hexane was investigated.","abstract_has_math":true,"creators":["Park, Yong Sun"],"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":2011,"date_issued":"2011-05-07T12:24:44Z","date_published":"2011-05-07T12:24:44Z","updated_at":"2026-07-22T22:25:15Z","subjects":["Chemistry, Organic"],"languages":["eng"],"rights":["Copyright 1996 Park, Yong Sun"],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["9780591089622","AAI9702635","(UMI)AAI9702635"],"render_values":[{"text":"9780591089622","href":null,"code":true},{"text":"AAI9702635","href":null,"code":true},{"text":"(UMI)AAI9702635","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/19974","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":["Park, Yong Sun"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2011-05-07T12:24:44Z","10000-01-01","1996"]},{"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"]},{"key":"dc:rights","label":"Dc Rights","values":["Copyright 1996 Park, Yong Sun"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["9780591089622","AAI9702635","(UMI)AAI9702635","http://hdl.handle.net/2142/19974"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["The lithiation-substitution of N-Boc benzylamines and cyclopropylamines have been investigated to explore the synthetic potential of these substrates. We have achieved the syntheses of highly enantioenriched benzylic $\\alpha$-substituted N-Boc secondary amines using RLi/(-)-sparteine. Extension of this chemistry to asymmetric syntheses of both enantiomers of primary $\\alpha$-substituted benzylamines and $\\alpha,\\alpha$-disubstituted benzylamines has been achieved successfully. Also, the N-Boc group was used as an activating and directing group for the $\\alpha$ and $\\beta$ lithiation-substitution of cyclopropanes. Extension of this chemistry to syntheses of highly functionalized cyclopentane by (3 + 2) cycloaddition and asymmetric synthesis of N-Boc azabicyclic (3.10) hexane was investigated.","Made available in DSpace on 2011-05-07T12:24:44Z (GMT). No. of bitstreams: 2 license.txt: 4922 bytes, checksum: 910b249b4beec47e7ab768910c8f966f (MD5) 9702635.pdf: 4376102 bytes, checksum: 8481d229ad9d77c9c327799f50581685 (MD5) Previous issue date: 1996","Item marked as restricted to the 'UIUC Users [automated]' Group (id=2) by Howard Ding (hding2@illinois.edu) on 2011-05-07T14:40:41Z Item is restricted indefinitely.","Restriction data tranferred 2014-07-01T11:17:29-05:00 Original Data Group with Access UIUC Users [automated] Release Date: none Reason: ETDs are only available to UIUC Users without author permission","ETDs are only available to UIUC Users without author permission","U of I Only"]},{"key":"dc:title","label":"Title","values":["Novel syntheses by directed lithiations of N-Boc benzylamines and cyclopropylamines"]}]}],"canonical_facts":{"dc:contributor":["Beak, Peter"],"dc:creator":["Park, Yong Sun"],"dc:date":["2011-05-07T12:24:44Z","10000-01-01","1996"],"dc:description":["The lithiation-substitution of N-Boc benzylamines and cyclopropylamines have been investigated to explore the synthetic potential of these substrates. We have achieved the syntheses of highly enantioenriched benzylic $\\alpha$-substituted N-Boc secondary amines using RLi/(-)-sparteine. Extension of this chemistry to asymmetric syntheses of both enantiomers of primary $\\alpha$-substituted benzylamines and $\\alpha,\\alpha$-disubstituted benzylamines has been achieved successfully. Also, the N-Boc group was used as an activating and directing group for the $\\alpha$ and $\\beta$ lithiation-substitution of cyclopropanes. Extension of this chemistry to syntheses of highly functionalized cyclopentane by (3 + 2) cycloaddition and asymmetric synthesis of N-Boc azabicyclic (3.10) hexane was investigated.","Made available in DSpace on 2011-05-07T12:24:44Z (GMT). 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