Item type:Thesis, Open Access

Flexible Synthese enantiomerenreiner 1,2-Diamine und 2,3-Diaminocarbonsäuren aus 1,2,5-Thiadiazol-1,1-dioxiden

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Date

2015-09-17

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Philipps-Universität Marburg
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Abstract

Chiral 1,2-diamines and 2,3-diamino carboxylic acids have attracted great deal of attention among organic chemists due to their numerous occurrence in natural products and biologically active compounds. Therefore, a novel method was developed,allowing to synthesize these two compound classes out of only one precursor, namely 1,2,5-thiadiazole-1,1-dioxides. In this thesis, an existing synthesis of 1,2-diamines out of 3,4-disubstituted 1,2,5-thiadiazole-1,1-dioxides was essentially improved regarding the enantiomeric excess of the formed diamines. In addition to that, a procedure for a stepwise protection of the two amino groups was developed, which facilitates to distinguish them chemically. In line with this investigation, it was shown, that 1,2,5-thiadiazole-1,1-dioxides can also serve as precursors for the synthesis of enantiopure a-tertiary 2,3-diamines, which implies the formation of a quaternary stereocenter. The synthesis of chiral 2,3-diamino carboxylic acids out of 1,2,5-thiadiazole-1,1-dioxides was solved by the use of 3-aryl-substituted 1,2,5-thiadiazole-1,1-dioxides as starting materials. Therefore, the aryl-substituent of the resulting chiral 1,2-diamines was oxidized to a carboxyl group.

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Dates
Created: 2015Issued: 2015-09-17
DOI
https://doi.org/10.17192/z2015.0385
Faculty
Fachbereich Chemie
Publisher
Philipps-Universität Marburg
Language
ger
Data types
DoctoralThesis
Keywords
thiadiazoletransfer hydrogenationdiamineaminocarboxylic acidenantioselective
DFG-subjects
DiamineThiadiazoleAminosäurenAsymmetrische SyntheseTransferhydrierung
DDC-Numbers
540
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https://rightsstatements.org/vocab/InC-NC/1.0/
URI
https://open.uni-marburg.de/handle/10.17192/z2015.0385
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Schüttler, Christian: Flexible Synthese enantiomerenreiner 1,2-Diamine und 2,3-Diaminocarbonsäuren aus 1,2,5-Thiadiazol-1,1-dioxiden. : Philipps-Universität Marburg 2015-09-17. DOI: https://doi.org/10.17192/z2015.0385.

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