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Stereoselective synthesis of 5-substituted pyrrolo[1,2-c]imidazol-3-ones. Access to aldosterone synthase inhibitors and chiral precatalysts

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dc.contributor.author Xu, Shufen
dc.date.accessioned 2010-10-26T14:59:59Z
dc.date.available 2010-10-26T14:59:59Z
dc.date.issued 2010-10-26
dc.identifier.uri http://hdl.handle.net/10464/3043
dc.description.abstract Compounds containing the pyrrolidine moiety are key substructures of compounds with biological activity and organocatalysts. In particular, annulated chiral pyrrolidines with alpha stereogenic centers have aldostereone synthase inhibition activity. In addition, 5-substituted pyrroloimidazol(in)ium salts precursors to N-heterocyclic carbene (NHC) precatalysts are rare due to a lack of convenient synthetic routes to access them. In this thesis is described a rapid synthesis of NHC precursors and a possible route to 5-substituted pyrroloimidazole biologically active compounds. The method involves the preparation of chiral saturated and achiral unsaturated pyrrolo[I,2- c]imidazol-3-ones from N-Cbz-protected t-Butyl proline carboxamide. The resulting starting materials may be used to prepare the target chiral annulated imidazol(in)ium products by a two-step sequence involving first stereoselective lithiation-substitution, followed by POCh induced salt formation. en_US
dc.language.iso eng en_US
dc.publisher Brock University en_US
dc.subject Organic compounds -- Synthesis en_US
dc.subject Aldosterone -- Synthesis en_US
dc.subject Pyrrolidine en_US
dc.title Stereoselective synthesis of 5-substituted pyrrolo[1,2-c]imidazol-3-ones. Access to aldosterone synthase inhibitors and chiral precatalysts en_US
dc.type Electronic Thesis or Dissertation en_US
dc.degree.name M.Sc. Biotechnology en_US
dc.degree.level Masters en_US
dc.contributor.department Centre for Biotechnology en_US
dc.degree.discipline Faculty of Mathematics and Science en_US


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