Akademik Veri Yönetim Sistemi
Tezin Türü: Yüksek Lisans
Tezin Yürütüldüğü Kurum: Orta Doğu Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Türkiye
Tezin Onay Tarihi: 2019
Öğrenci: Merve Bozdemir
Danışman: CİHANGİR TANYELİ
Özet:Organocatalytic asymmetric reactions are efficient and environmentally friendly methods to synthesize products with higher enantioselectivities. Asymmetric domino Michael-SN2 reactions are one of the type of organocatalytic reaction frequently used to form carbon-carbon bonds in the synthesis of the derivatives of dihydrofurans, which are intermediates mainly utilized as precessor materials in the pharmaceutical fields. In this thesis, the reaction occuring between acetylacetone and (Z)-(2-bromo-2-nitrovinyl)benzene was chosen as a model reaction. As a first step, bifunctional 2-aminoDMAP and quinine-anchored squaramide organocatalysts were tested. Then, quinine / t-butyl squaramide organocatalyst was identified as the most suitable organocatalyst for our reaction. Subsequently, optimization studies were done and using different α-bromonitroalkenes and 1,3-dicarbonyl compounds, 14 different derivatives were synthesized. In optimized conditions with 10 mol% organocatalyst loading, the best result gave 97 % enantiomeric excess.