Enantioselective michael addition of 1-nitropropane to nitroolefins with 2-aminodmap and quinine based bifunctional organocatalysts

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2015
Kanberoğlu, Esra
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
Citation Formats
E. Kanberoğlu, “Enantioselective michael addition of 1-nitropropane to nitroolefins with 2-aminodmap and quinine based bifunctional organocatalysts,” M.S. - Master of Science, Middle East Technical University, 2015.