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Title: Novel enantioselective construction of nitrocycloalkanes
Author: Sundaram , Rajkumar
Awarding Body: University of Reading
Current Institution: University of Reading
Date of Award: 2013
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This thesis studies the novel enantioselective of nitrocycloalkanes with multiple stereocentres via inter and/or intramolecular Michael addition using a variety of organocatalytic approaches. A novel nitro-Michael/Michael domino reaction catalysed by a quinine-derived bifunctional thiourea catalyst has been developed. This methodology has been applied to generate a variety of nitrocyclohexane derivatives, containing up to five contiguous stereocentres, with very high enantioselectivity and good diastereoselectivity. We have hypothesized that the reaction proceeds through the dual coordination of thiourea catalyst to both the nitronate and the conjugated ester. Finally the application of these compounds was demonstrated in the synthesis of a tetracyclic alkaloid a-lycorane-like compound. We have also successfully devised an enantioselective organocatlytic Michael addition to vinyl cyanosulfones catalysed by quinine-derive bifunctional thiourea catalyst. A variety of highly functionalised cyclohexyl derivatives containing one quaternary stereocentre in nature were synthesised with high yield and good enantioselectivity and diastereoselectivity. Finally, the synthetic application was demonstrated through the synthesis of and amino acid precursors.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available