{"id":{"repo_id":"aachen","oai_identifier":"oai:publications.rwth-aachen.de:62814"},"canonical_url":"https://search.dev.ndltd.org/etd/aachen/oai:publications.rwth-aachen.de:62814","repository":{"repo_id":"aachen","name":"RWTH Aachen University","base_url":"https://publications.rwth-aachen.de/oai2d"},"display":{"title":"Asymmetrische Synthese und stereoselektive Substitution allylischer Sulfoximin-funktionalisierter Homoallylalkohole","abstract":"Enantiopure acyclic (E)- and (Z)-configured allylic sulfoximines have been synthesized from N,S-dimethyl-S-phenylsulfoximine and aldehydes via the addition-elimination-isomerization route. Titanation of lithiated (E)- and (Z)-configured allylic sulfoximines with Chlortrisdiethylanimotitan and subsequent reaction with aldehydes afforded the corresponding alpha-syn-configured homoallylic alcohols with moderate to high regioselectivities and high diastereoselectivities. Copper-mediated subtitution in gamma position of the sulfonimidoyl-group furnished the corresponding (E)-configured allylic alcohols in good yields, with complete regioselectivities and high 1,3-chiraltiy transfer.","abstract_html":"Enantiopure acyclic (E)- and (Z)-configured allylic sulfoximines have been synthesized from N,S-dimethyl-S-phenylsulfoximine and aldehydes via the addition-elimination-isomerization route. Titanation of lithiated (E)- and (Z)-configured allylic sulfoximines with Chlortrisdiethylanimotitan and subsequent reaction with aldehydes afforded the corresponding alpha-syn-configured homoallylic alcohols with moderate to high regioselectivities and high diastereoselectivities. Copper-mediated subtitution in gamma position of the sulfonimidoyl-group furnished the corresponding (E)-configured allylic alcohols in good yields, with complete regioselectivities and high 1,3-chiraltiy transfer.","abstract_has_math":false,"creators":["Giesen, Nicole"],"institution":"Publikationsserver der RWTH Aachen University","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":["Gais, Hans-Joachim"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2001,"date_issued":"2001","date_published":"2001","updated_at":"2026-07-30T19:43:28Z","subjects":["info:eu-repo/classification/ddc/540","Chemie","Homoallyl-Verbindungen","Allylalkoholderivate","Sulfoximide","Asymmetrische Synthese","Hydroxyalkylierung","Substitutionsreaktion"],"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-124314%22"],"render_values":[{"text":"https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-124314%22","href":"https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-124314%22","code":true}]}]},"links":{"outbound_url":"https://publications.rwth-aachen.de/record/62814","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Gais, Hans-Joachim"]},{"key":"dc:creator","label":"Author","values":["Giesen, Nicole"]}]},{"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-2303"]},{"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","Homoallyl-Verbindungen","Allylalkoholderivate","Sulfoximide","Asymmetrische Synthese","Hydroxyalkylierung","Substitutionsreaktion"]}]},{"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/62814","https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-124314%22"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Enantiopure acyclic (E)- and (Z)-configured allylic sulfoximines have been synthesized from N,S-dimethyl-S-phenylsulfoximine and aldehydes via the addition-elimination-isomerization route. Titanation of lithiated (E)- and (Z)-configured allylic sulfoximines with Chlortrisdiethylanimotitan and subsequent reaction with aldehydes afforded the corresponding alpha-syn-configured homoallylic alcohols with moderate to high regioselectivities and high diastereoselectivities. Copper-mediated subtitution in gamma position of the sulfonimidoyl-group furnished the corresponding (E)-configured allylic alcohols in good yields, with complete regioselectivities and high 1,3-chiraltiy transfer."]},{"key":"dc:source","label":"Dc Source","values":["Aachen : Publikationsserver der RWTH Aachen University 142 S. (2001). = Aachen, Techn. Hochsch., Diss., 2001"]},{"key":"dc:title","label":"Title","values":["Asymmetrische Synthese und stereoselektive Substitution allylischer Sulfoximin-funktionalisierter Homoallylalkohole"]}]}],"canonical_facts":{"dc:contributor":["Gais, Hans-Joachim"],"dc:coverage":["DE"],"dc:creator":["Giesen, Nicole"],"dc:date":["2001"],"dc:description":["Enantiopure acyclic (E)- and (Z)-configured allylic sulfoximines have been synthesized from N,S-dimethyl-S-phenylsulfoximine and aldehydes via the addition-elimination-isomerization route. Titanation of lithiated (E)- and (Z)-configured allylic sulfoximines with Chlortrisdiethylanimotitan and subsequent reaction with aldehydes afforded the corresponding alpha-syn-configured homoallylic alcohols with moderate to high regioselectivities and high diastereoselectivities. Copper-mediated subtitution in gamma position of the sulfonimidoyl-group furnished the corresponding (E)-configured allylic alcohols in good yields, with complete regioselectivities and high 1,3-chiraltiy transfer."],"dc:identifier":["https://publications.rwth-aachen.de/record/62814","https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-124314%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-2303"],"dc:rights":["info:eu-repo/semantics/openAccess"],"dc:source":["Aachen : Publikationsserver der RWTH Aachen University 142 S. (2001). = Aachen, Techn. Hochsch., Diss., 2001"],"dc:subject":["info:eu-repo/classification/ddc/540","Chemie","Homoallyl-Verbindungen","Allylalkoholderivate","Sulfoximide","Asymmetrische Synthese","Hydroxyalkylierung","Substitutionsreaktion"],"dc:title":["Asymmetrische Synthese und stereoselektive Substitution allylischer Sulfoximin-funktionalisierter Homoallylalkohole"],"dc:type":["info:eu-repo/semantics/doctoralThesis","info:eu-repo/semantics/publishedVersion"]},"updated_at":"2026-07-30T19:43:28Z"}