{"id":{"repo_id":"aachen","oai_identifier":"oai:publications.rwth-aachen.de:50152"},"canonical_url":"https://search.dev.ndltd.org/etd/aachen/oai:publications.rwth-aachen.de:50152","repository":{"repo_id":"aachen","name":"RWTH Aachen University","base_url":"https://publications.rwth-aachen.de/oai2d"},"display":{"title":"Enantioselective synthesis of alkenyl aziridine carboxylates and 4-phenylsulfenyl prolines","abstract":"Chiral cyclic and acyclic allyl aminosulfoxonium ylides have been generated from aminosulfoxonium-substituted gamma,delta-unsaturated alpha-amino acids (method A) and 1-alkenyl aminosulfoxonium salts (method B) upon treatment with DBU. Their application to the asymmetric aziridination of N-tert-butyl-sulfonyl imino ester, generated either in situ (method A) or externally added (method B), gave the corresponding alkenyl aziridine carboxylates with medium to high diastereoselectivity and enantioselectivity. A highly stereoselective Pd(0)-catalyzed isomerization of an E,trans-configured alkenyl aziridine methanol derivative to its E-cis-isomer is described, which proceeded with retention of the double bond configuration. The Michael addition of thiophenol to aminosulfoxonium-substituted gamma,delta-unsaturated alpha-amino acids favours from Re-face. The resulted sulfides were applied to synthesize 4-phenylsulfenyl proline derivatives in overall good yields.","abstract_html":"Chiral cyclic and acyclic allyl aminosulfoxonium ylides have been generated from aminosulfoxonium-substituted gamma,delta-unsaturated alpha-amino acids (method A) and 1-alkenyl aminosulfoxonium salts (method B) upon treatment with DBU. Their application to the asymmetric aziridination of N-tert-butyl-sulfonyl imino ester, generated either in situ (method A) or externally added (method B), gave the corresponding alkenyl aziridine carboxylates with medium to high diastereoselectivity and enantioselectivity. A highly stereoselective Pd(0)-catalyzed isomerization of an E,trans-configured alkenyl aziridine methanol derivative to its E-cis-isomer is described, which proceeded with retention of the double bond configuration. The Michael addition of thiophenol to aminosulfoxonium-substituted gamma,delta-unsaturated alpha-amino acids favours from Re-face. The resulted sulfides were applied to synthesize 4-phenylsulfenyl proline derivatives in overall good yields.","abstract_has_math":false,"creators":["Iska, Vijaya Bhaskara Reddy"],"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":2008,"date_issued":"2008","date_published":"2008","updated_at":"2026-07-30T19:40:16Z","subjects":["info:eu-repo/classification/ddc/540","Asymmetrische Synthese","Chemie","Enantioselective synthesis","Alkenyl Aziridinecarboxylates","Proline"],"languages":["eng"],"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-112707%22"],"render_values":[{"text":"https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-112707%22","href":"https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-112707%22","code":true}]}]},"links":{"outbound_url":"https://publications.rwth-aachen.de/record/50152","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%3A50152","prefix":"oai_dc"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Gais, Hans-Joachim"]},{"key":"dc:creator","label":"Author","values":["Iska, Vijaya Bhaskara Reddy"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:coverage","label":"Dc Coverage","values":["DE"]},{"key":"dc:date","label":"Dc Date","values":["2008"]},{"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-24132"]},{"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","Asymmetrische Synthese","Chemie","Enantioselective synthesis","Alkenyl Aziridinecarboxylates","Proline"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]},{"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/50152","https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-112707%22"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Chiral cyclic and acyclic allyl aminosulfoxonium ylides have been generated from aminosulfoxonium-substituted gamma,delta-unsaturated alpha-amino acids (method A) and 1-alkenyl aminosulfoxonium salts (method B) upon treatment with DBU. Their application to the asymmetric aziridination of N-tert-butyl-sulfonyl imino ester, generated either in situ (method A) or externally added (method B), gave the corresponding alkenyl aziridine carboxylates with medium to high diastereoselectivity and enantioselectivity. A highly stereoselective Pd(0)-catalyzed isomerization of an E,trans-configured alkenyl aziridine methanol derivative to its E-cis-isomer is described, which proceeded with retention of the double bond configuration. The Michael addition of thiophenol to aminosulfoxonium-substituted gamma,delta-unsaturated alpha-amino acids favours from Re-face. The resulted sulfides were applied to synthesize 4-phenylsulfenyl proline derivatives in overall good yields."]},{"key":"dc:source","label":"Dc Source","values":["Aachen : Publikationsserver der RWTH Aachen University VIII, 150 S. (2008). = Aachen, Techn. Hochsch., Diss., 2008"]},{"key":"dc:title","label":"Title","values":["Enantioselective synthesis of alkenyl aziridine carboxylates and 4-phenylsulfenyl prolines"]}]}],"canonical_facts":{"dc:contributor":["Gais, Hans-Joachim"],"dc:coverage":["DE"],"dc:creator":["Iska, Vijaya Bhaskara Reddy"],"dc:date":["2008"],"dc:description":["Chiral cyclic and acyclic allyl aminosulfoxonium ylides have been generated from aminosulfoxonium-substituted gamma,delta-unsaturated alpha-amino acids (method A) and 1-alkenyl aminosulfoxonium salts (method B) upon treatment with DBU. Their application to the asymmetric aziridination of N-tert-butyl-sulfonyl imino ester, generated either in situ (method A) or externally added (method B), gave the corresponding alkenyl aziridine carboxylates with medium to high diastereoselectivity and enantioselectivity. A highly stereoselective Pd(0)-catalyzed isomerization of an E,trans-configured alkenyl aziridine methanol derivative to its E-cis-isomer is described, which proceeded with retention of the double bond configuration. The Michael addition of thiophenol to aminosulfoxonium-substituted gamma,delta-unsaturated alpha-amino acids favours from Re-face. The resulted sulfides were applied to synthesize 4-phenylsulfenyl proline derivatives in overall good yields."],"dc:identifier":["https://publications.rwth-aachen.de/record/50152","https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-112707%22"],"dc:language":["eng"],"dc:publisher":["Publikationsserver der RWTH Aachen University"],"dc:relation":["info:eu-repo/semantics/altIdentifier/urn/urn:nbn:de:hbz:82-opus-24132"],"dc:rights":["info:eu-repo/semantics/openAccess"],"dc:source":["Aachen : Publikationsserver der RWTH Aachen University VIII, 150 S. (2008). = Aachen, Techn. Hochsch., Diss., 2008"],"dc:subject":["info:eu-repo/classification/ddc/540","Asymmetrische Synthese","Chemie","Enantioselective synthesis","Alkenyl Aziridinecarboxylates","Proline"],"dc:title":["Enantioselective synthesis of alkenyl aziridine carboxylates and 4-phenylsulfenyl prolines"],"dc:type":["info:eu-repo/semantics/doctoralThesis","info:eu-repo/semantics/publishedVersion"]},"updated_at":"2026-07-30T19:40:16Z"}