dc.contributor.authorHuang, Zhijian
dc.date.accessioned2016-11-14T01:27:23Z
dc.date.available2016-11-14T01:27:23Z
dc.date.issued2016
dc.identifier.citationHuang, Z. (2016). Asymmetric reactions of unsaturated esters and desymmetrizations of P-stereogenic phosphinates via carbene catalysis and oxidative carbene catalysis. Doctoral thesis, Nanyang Technological University, Singapore.
dc.identifier.urihttp://hdl.handle.net/10356/69156
dc.description.abstractThis thesis focuses on esters activation and desymmetrization for enantioselective reactions enabled by N-heterocyclic carbenes (NHCs) organocatalysts. It contains four parts: Chapter 1 gives brief introductions to the history and development of NHC catalysis classified by common active intermediates within this field. Representative examples and furture challenges are summarized and reviewed as well in this part. Chapter 2 describes a formal LUMO activation of α, β-unsaturated esters enabled by NHC catalyst for highly enantioselective lactam formation. Sterically bulky β, β-disubstituted esters can also be used in this strategy, which delivers the optically enriched product containing a quarternary carbon center. Chapter 3 is about NHC-catalyzed cascade reaction for synthesis of functionalized pyrrolo[3,2-c]quinolones. The products from Michael-Mannich-Lactamization cascade reaction are obtained in good yield and enantioselectivity with three consecutive stereogenic centers. Chapter 4 introduces a rapid approach to P-stereogenic phosphinates via NHC-catalyzed desymmetrization of bisphenols. Due to the high efficiency of the reaction, the enantiomerically enriched P-stereogenic phosphinates can be prepared in large scale under low catalyst loading. The chiral phosphinates are also demonstrated as a good catalyst in the reductive aldol reaction.en_US
dc.format.extent134 p.en_US
dc.language.isoenen_US
dc.subjectDRNTU::Scienceen_US
dc.titleAsymmetric reactions of unsaturated esters and desymmetrizations of P-stereogenic phosphinates via carbene catalysis and oxidative carbene catalysisen_US
dc.typeThesis
dc.contributor.supervisorYonggui Robin Chien_US
dc.contributor.schoolSchool of Physical and Mathematical Sciencesen_US
dc.description.degreeDoctor of Philosophy (SPMS)en_US


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