Improving Asymmetric Decarboxylative Aldol Reaction and Synthesis of TPT-Acetylene Matrix

Güler, Hande
In recent years, studies, and the use of organocatalysts have increased considerably. Unlike metal catalysts, non-toxic, robust organocatalysts have ensured their usability in many organic reactions. In this work, a new sulfonamide type bifunctional organocatalyst was synthesized and used in the asymmetric reaction. First, the decarboxylative aldol reaction of α-amidohemimalonates with aldehydes was studied in the presence of a bifunctional organocatalyst. An optimization study of this reaction was performed to enhance the enantioselectivity and diastereoselectivity. Racemic and chiral products of decarboxylative aldol reaction were synthesized with α-amidohemimalonate and 4-nitrobenzaldehyde. The structure elucidation of the product was done with NMR spectroscopy, and the selectivities were determined with HPLC. The second part of the thesis involves a different aspect of organocatalysts' usage. Because of high catalyst loading requirements or difficulties in catalyst recovery and reuse in organocatalysis, these catalysts have limited practical applicability. In this context, the immobilization of organocatalysts on solid supports has emerged as a promising strategy to avoid these limitations. In this project, various thiophene-pyrrole-thiophene (TPT) host systems that are able to anchor proper organocatalysts were synthesized. To reach the TPT product, 1-(thiophen-2-yl)-4-(thiophen-3-yl)butane-1,4-dione (the diketone precursor) was synthesized first. Then, the TPT products were manufactured. The TPT monomer was polymerized and proved to become a reusable organocatalysts' matrix.


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Citation Formats
H. Güler, “Improving Asymmetric Decarboxylative Aldol Reaction and Synthesis of TPT-Acetylene Matrix,” M.S. - Master of Science, Middle East Technical University, 2022.