Enantioselective synthesis of cyclic beta-amino alcohols via tandem hydroalumination-cyclization-reduction of ethoxycarbonyl vinyl sulfoximines and application to the synthesis of potential aggrecanase inhibitors

The beta-amino alcohol moiety is a common structural component in a wide variety of natural occurring compounds, synthetic pharmacologically important molecules, ligands and chiral auxiliaries for asymmetric synthesis. Due to the fact that the stereochemistry of the beta-amino alcohol moiety is important for biological activity and for chirality transfer, asymmetric synthesis of compounds containing beta-amino alcohol functionality has drawn considerable attention. This thesis describes enantioselective synthesis of cyclic beta-amino alcohols starting from ethoxycarbonyl vinyl sulfoximines, which are prepared from cyclic bis(allylsulfoximine)titanium complexes and N-tert-butylsulfonyl alpha-imino ester. The application of sulfoximine substituted bicyclic 1,2-amino alcohol in the synthesis of potential aggrecanase inhibitor is described.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2009

Author dc:creator

• Acikalin, Serdar

Contributors dc:contributor

• Gais, Hans-Joachim

• info:eu-repo/classification/ddc/540
• Asymmetrische Synthese
• Sulfoximin
• Alkanolamine
• Chemie
• zyklische beta-Aminoalkohole
• Hydroaluminierung
• Aggrecanase-Inhibitor
• asymmetric synthesis
• sulfoximine
• cyclic beta-aminoalcohols
• hydroalumination

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

eng

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-113674%22

OAI record oai:identifier

https://publications.rwth-aachen.de/oai2d?verb=GetRecord&metadataPrefix=oai_dc&identifier=oai%3Apublications.rwth-aachen.de%3A51375