{"id":{"repo_id":"aachen","oai_identifier":"oai:publications.rwth-aachen.de:56490"},"canonical_url":"https://search.dev.ndltd.org/etd/aachen/oai:publications.rwth-aachen.de:56490","repository":{"repo_id":"aachen","name":"RWTH Aachen University","base_url":"https://publications.rwth-aachen.de/oai2d"},"display":{"title":"Neue Ankergruppen für die enantioselektive kombinatorische Festphasensynthese","abstract":"Within the scope of this work three new linkers for solid phase synthesis have been developed. Starting with functionalized amines these were diazotated and coupled onto a resin with secondary amine functionalities. This triazene-linker (T1-linker) allows the traceless cleavage of arenes. On the T1-linker Heck-reactions and based upon this several further derivatisations have been realized. Furthermore a linker system for the coupling of amines based on immobilized diazonium salts has been developed (T2-linker). On the T2-linker piperidone has successfully been immobilized, as a central building block for the sysnthesis of analgetics in cooperation with the Grünenthal-GmbH. On this building block Mannich-, Grignard- and Wittig-reactions have been realized, leading to precursors of the desired substances. In order to synthesize a \"SAMP-resin\", a trityl-protected precursor was synthesized from trans-4-Hydroxy-L-proline and linked to Merrifieldïs-resin. Deprotection, nitrosation and reduction lead to the \"SAMP-resin\". Hydrazones based on this \"SAMP-resin\" were used in alpha-alkylations at -100 øC leading to ee- values up to 86.3%. A library of 24 chiral ketones was synthesized at -72 øC. The purities of the products exeeded 99% and they showed moderate ee-values of up to 78.6%.","abstract_html":"Within the scope of this work three new linkers for solid phase synthesis have been developed. Starting with functionalized amines these were diazotated and coupled onto a resin with secondary amine functionalities. This triazene-linker (T1-linker) allows the traceless cleavage of arenes. On the T1-linker Heck-reactions and based upon this several further derivatisations have been realized. Furthermore a linker system for the coupling of amines based on immobilized diazonium salts has been developed (T2-linker). On the T2-linker piperidone has successfully been immobilized, as a central building block for the sysnthesis of analgetics in cooperation with the Grünenthal-GmbH. On this building block Mannich-, Grignard- and Wittig-reactions have been realized, leading to precursors of the desired substances. In order to synthesize a "SAMP-resin", a trityl-protected precursor was synthesized from trans-4-Hydroxy-L-proline and linked to Merrifieldïs-resin. Deprotection, nitrosation and reduction lead to the "SAMP-resin". Hydrazones based on this "SAMP-resin" were used in alpha-alkylations at -100 øC leading to ee- values up to 86.3%. A library of 24 chiral ketones was synthesized at -72 øC. The purities of the products exeeded 99% and they showed moderate ee-values of up to 78.6%.","abstract_has_math":false,"creators":["Köbberling, Johannes"],"institution":"Publikationsserver der RWTH Aachen University","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":["Enders, Dieter"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2001,"date_issued":"2001","date_published":"2001","updated_at":"2026-07-30T19:41:53Z","subjects":["info:eu-repo/classification/ddc/540","Chemie","Ankergruppe","Kombinatorische Synthese","Asymmetrische Synthese","Festphasentechnik"],"languages":["ger"],"rights":["info:eu-repo/semantics/openAccess"],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-118587%22"],"render_values":[{"text":"https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-118587%22","href":"https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-118587%22","code":true}]}]},"links":{"outbound_url":"https://publications.rwth-aachen.de/record/56490","outbound_label":"Repository record","outbound_source":"dc:identifier"},"source_record":{"url":"https://publications.rwth-aachen.de/oai2d?verb=GetRecord&metadataPrefix=oai_dc&identifier=oai%3Apublications.rwth-aachen.de%3A56490","prefix":"oai_dc"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Enders, Dieter"]},{"key":"dc:creator","label":"Author","values":["Köbberling, Johannes"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:coverage","label":"Dc Coverage","values":["DE"]},{"key":"dc:date","label":"Dc Date","values":["2001"]},{"key":"dc:publisher","label":"Institution","values":["Publikationsserver der RWTH Aachen University"]},{"key":"dc:relation","label":"Dc Relation","values":["info:eu-repo/semantics/altIdentifier/urn/urn:nbn:de:hbz:82-opus-1493"]},{"key":"dc:type","label":"Dc Type","values":["info:eu-repo/semantics/doctoralThesis","info:eu-repo/semantics/publishedVersion"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["info:eu-repo/classification/ddc/540","Chemie","Ankergruppe","Kombinatorische Synthese","Asymmetrische Synthese","Festphasentechnik"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["ger"]},{"key":"dc:rights","label":"Dc Rights","values":["info:eu-repo/semantics/openAccess"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://publications.rwth-aachen.de/record/56490","https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-118587%22"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Within the scope of this work three new linkers for solid phase synthesis have been developed. Starting with functionalized amines these were diazotated and coupled onto a resin with secondary amine functionalities. This triazene-linker (T1-linker) allows the traceless cleavage of arenes. On the T1-linker Heck-reactions and based upon this several further derivatisations have been realized. Furthermore a linker system for the coupling of amines based on immobilized diazonium salts has been developed (T2-linker). On the T2-linker piperidone has successfully been immobilized, as a central building block for the sysnthesis of analgetics in cooperation with the Grünenthal-GmbH. On this building block Mannich-, Grignard- and Wittig-reactions have been realized, leading to precursors of the desired substances. In order to synthesize a \"SAMP-resin\", a trityl-protected precursor was synthesized from trans-4-Hydroxy-L-proline and linked to Merrifieldïs-resin. Deprotection, nitrosation and reduction lead to the \"SAMP-resin\". Hydrazones based on this \"SAMP-resin\" were used in alpha-alkylations at -100 øC leading to ee- values up to 86.3%. A library of 24 chiral ketones was synthesized at -72 øC. The purities of the products exeeded 99% and they showed moderate ee-values of up to 78.6%."]},{"key":"dc:source","label":"Dc Source","values":["Aachen : Publikationsserver der RWTH Aachen University IV, 226 S. : Ill., graph. Darst. (2001). = Aachen, Techn. Hochsch., Diss., 2001"]},{"key":"dc:title","label":"Title","values":["Neue Ankergruppen für die enantioselektive kombinatorische Festphasensynthese"]}]}],"canonical_facts":{"dc:contributor":["Enders, Dieter"],"dc:coverage":["DE"],"dc:creator":["Köbberling, Johannes"],"dc:date":["2001"],"dc:description":["Within the scope of this work three new linkers for solid phase synthesis have been developed. Starting with functionalized amines these were diazotated and coupled onto a resin with secondary amine functionalities. 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The purities of the products exeeded 99% and they showed moderate ee-values of up to 78.6%."],"dc:identifier":["https://publications.rwth-aachen.de/record/56490","https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-118587%22"],"dc:language":["ger"],"dc:publisher":["Publikationsserver der RWTH Aachen University"],"dc:relation":["info:eu-repo/semantics/altIdentifier/urn/urn:nbn:de:hbz:82-opus-1493"],"dc:rights":["info:eu-repo/semantics/openAccess"],"dc:source":["Aachen : Publikationsserver der RWTH Aachen University IV, 226 S. : Ill., graph. Darst. (2001). = Aachen, Techn. Hochsch., Diss., 2001"],"dc:subject":["info:eu-repo/classification/ddc/540","Chemie","Ankergruppe","Kombinatorische Synthese","Asymmetrische Synthese","Festphasentechnik"],"dc:title":["Neue Ankergruppen für die enantioselektive kombinatorische Festphasensynthese"],"dc:type":["info:eu-repo/semantics/doctoralThesis","info:eu-repo/semantics/publishedVersion"]},"updated_at":"2026-07-30T19:41:53Z"}