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Stereoselective mannich reactions of mono thiomalonates : & screening for peptidic triazolium salt based catalysts

Bahlinger, Annette. Stereoselective mannich reactions of mono thiomalonates : & screening for peptidic triazolium salt based catalysts. 2014, PhD Thesis, University of Basel, Faculty of Science.

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Official URL: http://edoc.unibas.ch/diss/DissB_11115

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Abstract

Part I: The stereoselective synthesis of ß-amino thioesters is of high interest since they are versatile and common building blocks for a variety of pharmaceutically important compounds. Within this thesis a mild organocatalyzed approach for the synthesis of ß-amino thioesters by using mono thiomalonates (MTMs) as thioester enolate equivalents was developed. Those nucleophiles proved to be highly reactive in Mannich reactions providing for acyclic ß2-amino thioesters and ß2,3,3-amino thioesters with adjacent tertiary and quaternary stereocenters in high yields and excellent stereoselectivities. In addition, the synthetic value of ß-amino thioesters as building blocks for coupling-agent-free liquid phase, as well as solid phase peptide synthesis was shown.
Part II: In the second part of this thesis the combinatorial approach of encoded one-bead-one-compound libraries was successfully used to identify bifunctional peptidic N-heterocyclic carbene catalysts for the redox amidation reaction of aldehydes and amines.
Advisors:Wennemers, Helma
Committee Members:Pfaltz, Andreas
Faculties and Departments:05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Bioorganische Chemie (Wennemers)
Item Type:Thesis
Thesis no:11115
Bibsysno:Link to catalogue
Number of Pages:187 p.
Language:English
Identification Number:
Last Modified:30 Jun 2016 10:57
Deposited On:27 Mar 2015 08:55

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