Fluorous Organocatalysis in Green Medicinal Chemistry

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Presentation transcript:

Fluorous Organocatalysis in Green Medicinal Chemistry Synthesis of Spirocyclic Oxindoles Uriel Tayvah

Zhang Lab Medicinal chemistry Asymmetric organocatalysis Fluorine chemistry

Recyclable Fluorous Organocatalysis Fluorous Solid-Phase Extraction (F-SPE) Allows catalyst to be reused (~96% recovery) Graphic by Xin Huang

Recyclable Fluorous Organocatalysis (cont.) Examples of fluorous organocatalysts Effective for certain asymmetric Michael additions1 cat-1 1Huang, X.; Yi, W. B.; Ahad, D.; Zhang, W. Tetrahedron Lett. 2013, 54, 6064-6066.

Spirocyclic Oxindoles with chiral centers Structure found in many biologically active compounds Can be synthesized via asymmetric Michael additions using cat-1

Separation/purification Research process Testing reactions Optimizing reaction conditions Set-up Characterization Separation/purification Microwave synthesizer Liquid chomatography-mass spectrometer (LC-MS) High performance liquid chromatograph (HPLC) Photos by Cecilia Clamens

Reflections Window into research process/lab environment Learned about instruments and the basics of lit. review

Acknowledgments Thanks to PEI, Prof. Wei Zhang, Xin Huang, Cecilia Clamens, and Kenny Pham.