Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/32348
Title: Direct Asymmetric Vinylogous Reactions of Furanones and Phthalide Derivatives with Bifunctional and Trifunctional Organocatalysts
Authors: LUO JIE
Keywords: organocatalysis, vinylogous reaction, furanones, phthalide derivatives, bifunctional organocatalyst, trifunctional organocatalyst
Issue Date: 2-Aug-2011
Source: LUO JIE (2011-08-02). Direct Asymmetric Vinylogous Reactions of Furanones and Phthalide Derivatives with Bifunctional and Trifunctional Organocatalysts. ScholarBank@NUS Repository.
Abstract: The research aim of this thesis is to develop direct enantioselective vinylogous reactions of furanones and phthalide derivatives with bifunctional and trifunctional organocatalysts. Firstly, the direct asymmetric vinylogous aldol reaction of furanones with a-ketoesters will be demonstrated using L-tryptophan derived bifunctional thiourea catalyst. The synthetic method provides an easy access to biologically important r-substituted butenolides and chiral glycerol derivatives. In the second part, asymmetric mannich reaction of phthalide derivatives will be shown employing a cinchona derived trifunctional catalyst. The mannich adduct could be easily transformed into chiral substituted isoquinolines and isoquinolinones. Lastly, the highly diastereoselective and enantioselective Michael addition of phthalide derivatives to nitroolefins and chalcones will be discussed, which allows a facial generation of biologically important substituted phthalides.
URI: http://scholarbank.nus.edu.sg/handle/10635/32348
Appears in Collections:Ph.D Theses (Open)

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