Neue Ankergruppen für die enantioselektive kombinatorische Festphasensynthese

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%.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2001

Author dc:creator

• Köbberling, Johannes

Contributors dc:contributor

• Enders, Dieter

• info:eu-repo/classification/ddc/540
• Chemie
• Ankergruppe
• Kombinatorische Synthese
• Asymmetrische Synthese
• Festphasentechnik

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

ger

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-118587%22

OAI record oai:identifier

https://publications.rwth-aachen.de/oai2d?verb=GetRecord&metadataPrefix=oai_dc&identifier=oai%3Apublications.rwth-aachen.de%3A56490