Synthese neuartiger Sulfonimidamide zur Anwendung in der asymmetrischen Katalyse

In the context of this research the synthesis of novel sulfonimidamides and their modification was envisaged with regard to their application in asymmetric catalysis. The first part of this work was dedicated to the synthesis of these highly oxidized sulfur compounds. Starting from sulfinic acid sodium salt and arylthiols, respectively, racemic and enantiopure sulfonimidamides were accessible utilizing mainly two different protocols. In the second part the modification of the amide-nitrogen atom was examined. Therefore, the sulfonimidamides were reacted with uronium reagents to give highly functionalized sulfonimidoylguanidines in up to quantitative yields while the configuration at the sulfur atom is retained. Moreover, a copper-mediated cross coupling reaction for the preparation of N-arylated sulfonimidamides was developed. The products were obtained in moderate to good yields in the presence of stoichiometric amounts of copper(I) salt, potassium carbonate and aryliodides or -bromides. In the last part of the thesis the synthesis of prolyl sulfonimidamides is described and their applicability as potent organocatalysts in the solvent-free asymmetric aldol reaction has been demonstrated.

Grantor dc:publisher

Sierke

Year dc:date

2009

Author dc:creator

• Worch, Christin

Contributors dc:contributor

• Bolm, Carsten

• info:eu-repo/classification/ddc/540
• Katalyse
• Organokatalyse
• Schwefel
• Chemie
• Sulfonimidamid
• asymmetrische Katalyse
• Sulfinamid
• sulfonimidamide
• asymmetric catalysis
• sulfinamide
• organocatalysis
• sulfur

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

ger

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-113673%22

OAI record oai:identifier

https://publications.rwth-aachen.de/oai2d?verb=GetRecord&metadataPrefix=oai_dc&identifier=oai%3Apublications.rwth-aachen.de%3A51372