Enantioselective michael addition of 1-nitropropane to nitroolefins with 2-aminodmap and quinine based bifunctional organocatalysts
Tez Türü: Yüksek Lisans
Tezin Yürütüldüğü Kurum: Orta Doğu Teknik Üniversitesi, Fen Bilimleri Enstitüsü, Kimya , Türkiye
Tez Danışmanı: Cihangir Tanyeli
Tezin Onay Tarihi: 2015
Tezin Dili: İngilizce
Özet:
1,3-dinitro compounds are key materials in the synthesis of a variety of important fine
chemicals. Moreover, they are reduced to 1,3-diamines which are starting materials of
biologically active compounds, agrochemicals and pharmaceuticals. In this study,
((2S,3S)-1,3-dinitropentan-2-yl)benzene was synthesized via the Michael addition of
1-nitropropane to trans-β-nitrostyrene in the presence of chiral bifunctional 2-
aminoDMAP and quinine based organocatalysts. In the first part of study, reaction
conditions were optimized by testing all organocatalysts and changing the solvent,
temperature, catalyst loading as well as concentration. After getting the optimized
condition for this reaction, derivatization studies were conducted with various
nitroolefins. Excellent enantioselectivities up to 95% and high diastereoselectivities
such as 96:4 were obtained in the desired 1,3-dinitro compounds.