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postgraduate thesis: Chiral phosphonium ion tagged and spiroindane-based organocatalysts

TitleChiral phosphonium ion tagged and spiroindane-based organocatalysts
Authors
Issue Date2011
PublisherThe University of Hong Kong (Pokfulam, Hong Kong)
Citation
Hermeke, J.. (2011). Chiral phosphonium ion tagged and spiroindane-based organocatalysts. (Thesis). University of Hong Kong, Pokfulam, Hong Kong SAR. Retrieved from http://dx.doi.org/10.5353/th_b4729568
AbstractThe research on asymmetric organocatalysis has been intensifying since the beginning of 2000. The growing interest in this research area is driven by the importance of the chemical synthesis of enantiomerically pure products. While the general field of asymmetric organocatalysis has been explored intensively, the recyclability of organocatalysts has not really been considered. The attachment of phosphonium ion phase tags to chiral binaphthyl-based phosphoric acid catalyst and the use of these materials in a range of organocatalytic asymmetric Friedel-Crafts reactions of indoles have been studied. Placement of tags at the 3 and 3’ positions of the binaphthyl core, so that they could serve as steric blocking groups, failed to produce an active catalyst. However, moving the phosphonium ion groups to the 6 and 6’ positions produced an efficient and enantioselective catalyst. Aided by the presence of the phase tags, the chiral catalyst was easily recovered at the end of the reactions, and could be reused several times, albeit with somewhat decreased efficiency and enantioselectivity. Furthermore, the synthesis of 1,1’-spirobiindane-7,7’-diol and their spiroindane-based derivatives have been explored. The (R)-1,1’-spirobiindane- 7,7’-diamine was successfully applied in exo selective asymmetric Diels-Alder reactions of -unsaturated aldehyde with cyclopentadiene. However, moderate results aspire further studies in assay of (R)-1,1’-spirobiindane-7,7’-diamine derivatives, which bear various bulky groups at the 6 and 6’ positions. Moreover, the conversion of the SPINOL into a spiroindane ketone unfortunately failed, which was caused by the sterically crowded structure of the SPINOL skeleton.
DegreeMaster of Philosophy
SubjectOrganic compounds - Synthesis
Asymmetric synthesis
Catalysis
Dept/ProgramChemistry
Persistent Identifierhttp://hdl.handle.net/10722/205871

 

DC FieldValueLanguage
dc.contributor.authorHermeke, Julia-
dc.date.accessioned2014-10-17T23:13:56Z-
dc.date.available2014-10-17T23:13:56Z-
dc.date.issued2011-
dc.identifier.citationHermeke, J.. (2011). Chiral phosphonium ion tagged and spiroindane-based organocatalysts. (Thesis). University of Hong Kong, Pokfulam, Hong Kong SAR. Retrieved from http://dx.doi.org/10.5353/th_b4729568-
dc.identifier.urihttp://hdl.handle.net/10722/205871-
dc.description.abstractThe research on asymmetric organocatalysis has been intensifying since the beginning of 2000. The growing interest in this research area is driven by the importance of the chemical synthesis of enantiomerically pure products. While the general field of asymmetric organocatalysis has been explored intensively, the recyclability of organocatalysts has not really been considered. The attachment of phosphonium ion phase tags to chiral binaphthyl-based phosphoric acid catalyst and the use of these materials in a range of organocatalytic asymmetric Friedel-Crafts reactions of indoles have been studied. Placement of tags at the 3 and 3’ positions of the binaphthyl core, so that they could serve as steric blocking groups, failed to produce an active catalyst. However, moving the phosphonium ion groups to the 6 and 6’ positions produced an efficient and enantioselective catalyst. Aided by the presence of the phase tags, the chiral catalyst was easily recovered at the end of the reactions, and could be reused several times, albeit with somewhat decreased efficiency and enantioselectivity. Furthermore, the synthesis of 1,1’-spirobiindane-7,7’-diol and their spiroindane-based derivatives have been explored. The (R)-1,1’-spirobiindane- 7,7’-diamine was successfully applied in exo selective asymmetric Diels-Alder reactions of -unsaturated aldehyde with cyclopentadiene. However, moderate results aspire further studies in assay of (R)-1,1’-spirobiindane-7,7’-diamine derivatives, which bear various bulky groups at the 6 and 6’ positions. Moreover, the conversion of the SPINOL into a spiroindane ketone unfortunately failed, which was caused by the sterically crowded structure of the SPINOL skeleton.-
dc.languageeng-
dc.publisherThe University of Hong Kong (Pokfulam, Hong Kong)-
dc.relation.ispartofHKU Theses Online (HKUTO)-
dc.rightsCreative Commons: Attribution 3.0 Hong Kong License-
dc.rightsThe author retains all proprietary rights, (such as patent rights) and the right to use in future works.-
dc.subject.lcshOrganic compounds - Synthesis-
dc.subject.lcshAsymmetric synthesis-
dc.subject.lcshCatalysis-
dc.titleChiral phosphonium ion tagged and spiroindane-based organocatalysts-
dc.typePG_Thesis-
dc.identifier.hkulb4729568-
dc.description.thesisnameMaster of Philosophy-
dc.description.thesislevelMaster-
dc.description.thesisdisciplineChemistry-
dc.description.naturepublished_or_final_version-
dc.identifier.doi10.5353/th_b4729568-
dc.date.hkucongregation2011-

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