The enantioselective synthesis of 2-indolyl-1-nitro derivatives and BODIPY dyes in the presence of chiral bifunctional squaramide organocatalysts

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2022-8

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Dündar, Esra

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In our research group, chiral bifunctional squaramides with different basic units have been synthesized and evaluated in various asymmetric reactions. To test the catalytic activity of organocatalysts, Friedel-Crafts alkylation of indoles with nitroolefins was selected as a model reaction in the first part of the study. 19 different 2-indolyl-1-nitro derivatives were synthesized with up to >99% ee in the presence of sterically encumbered tert-butyl substituted squaramide/quinine. Besides, 2-adamantyl squaramide/quinine was evaluated in the addition of BODIPY core to isatin derivatives which will be the first example of this kind of enantioselective addition in literature. 6 novel chiral BODIPY dyes were synthesized with up to 60% ee, and their spectroscopic and chiroptical properties were investigated. In the final chapter, a point chiral at boron and carbon BODIPY was synthesized with a two-pot, one-step synthesis-an interrupted Knoevenagel condensation. ECD spectra of the dye showed a strong Cotton effect in the visible region. However, this dye showed weak fluorescence emission due to partly vibrational relaxations and bent-shaped molecular geometry.

Subject Keywords

Enantioselective Synthesis, Organocatalysis, Friedel-Crafts Alkylation, BODIPY Dyes, Squaramides

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https://hdl.handle.net/11511/98642

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

E. Dündar, “The enantioselective synthesis of 2-indolyl-1-nitro derivatives and BODIPY dyes in the presence of chiral bifunctional squaramide organocatalysts,” Ph.D. - Doctoral Program, Middle East Technical University, 2022.