Date of Award
8-31-2018
Document Type
Campus Access Thesis
Degree Name
Master of Science (MS)
Department
Chemistry/Organic Chemistry
First Advisor
Wei Zhang
Second Advisor
Niya Sa
Third Advisor
Neil Reilly
Abstract
Spirooxindole is a biologically interested scaffold which can be found in many natural products and medicinal chemicals, such as horsfiline, elacomine, spirotryprostatin A, MDM2 inhibitor pteropodine, antibacterial agent and antimalarial drug NITD609. Described in this thesis are the development of new projects for pot-economic synthesis of spirooxindoles via recyclable organocatalyst-promoted asymmetric synthesis and montmorillonite K10-catalyzed diastereoselective synthesis, which include: (1) organocatalytic and asymmetric synthesis of thiolated spiro-γ-lactam-oxindoles bearing three stereocenters; (2) organocatalytic and asymmetric synthesis of dihydrofuranone and tetrahydropyran spirooxindoles; (3) regio/diastereoselective synthesis of polyheterocyclic-fused spirooxindoles via α-C-H functionalization of cyclic amines. All these projects were developed as one-pot synthesis and using reusable fluorous bifunctional cinchona alkaloid-thiourea catalyst or solid montmorillonite K10 as Brønsted acid catalyst. The new methods are highly efficient and have good stereochemistry selectivities. Green chemistry techniques such as pot, atom and step economy (PASE) synthesis, minimal intermediate separation, free of toxic transition metal catalysts, and catalyst recovery are integrated to the projects.
Recommended Citation
Liu, Miao, "Asymmetric Organocatalysis and Pot Economic Synthesis of Heterocyclic Compounds" (2018). Graduate Masters Theses. 505.
https://scholarworks.umb.edu/masters_theses/505
Comments
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