Abstract
dc:descriptionThis thesis describes the synthesis of novel heterocyclic sulfoximines. Being aware the enormous application potential of heterocyclic sulfoximines (e.g. as bioactive compounds or as ligands), we were inspired to expand the existing protocols for the synthesis of this class of compounds. In the first part of the thesis the regioselective synthesis of sulfoximidoyl-1,2,3-triazoles is described. Sulfoximidoyl-alkynes with various substitution patterns were synthesized and were used as substrates in Huisgen-1,3-dipolar cycloaddition reactions with organic azides. The corresponding sulfoximidoyl-1,2,3-triazoles were obtained in yields up to 73%. The regioselectivities were examined by use of 1H-NOESY-spectroscopy. It became apparent that only 1,4-disubstituted (referring to the azide substituent and the sulfoximidoyl group) regioisomers could be isolated. Moreover, chiral sulfoximidoyl-1,2,3-triazoles were prepared from N-propargyl-sulfoximines and organic azides in yields up to 92% and with excellent regioselectivities. The second part of the thesis describes the investigation of the ring-closing enyne metathesis (RCEYM) reaction of doubly unsaturated sulfoximines leading to heterocyclic sulfoximines. It soon became apparent that the outcome of this reaction is highly dependent on the substrate structure (such as substitution pattern and tether length). By use of RCEYM reactions, seven-membered heterocyclic sulfoximines could be synthesized in yields up to 79%. These heterocyclic products were converted to tricyclic sulfoximines in yields up to 99% by sequential Diels-Alder-reactions and aromatizations.
Degree
thesis:*- Grantor dc:publisher
- Publikationsserver der RWTH Aachen University
- Year dc:date
- 2009
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Füger, Bernhard
- Contributors dc:contributor
-
- Bolm, Carsten
Subjects
dc:subject × 15Rights
dc:rights- Statement dc:rights
-
- info:eu-repo/semantics/openAccess
- Language dc:language
- ger