Date of Award


Document Type

Campus Access Thesis

Degree Name

Master of Science (MS)


Chemistry/Organic Chemistry

First Advisor

Wei Zhang

Second Advisor

Niya Sa

Third Advisor

Neil Reilly


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.


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