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

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


İPEK, HALİL; Akdağ, Akın (Informa UK Limited, 2015-08-03)
Chiral sulfoxides are used in asymmetric synthesis and are present in various biologically active compounds. Asymmetric synthesis of the sulfoxides has been performed by chiral metal complexes and non-metals containing peroxide and oxide moieties. In this study, a new metal free method has been developed to oxidize thioanisole into methyl phenyl sulfoxide with easily accessible chiral compounds carrying N-Cl bond. For this purpose, chiral amine and amide bearing reagents were synthesized and chlorinated by ...
Formaldehyde Selectivity in Methanol Partial Oxidation on Silver: Effect of Reactive Oxygen Species, Surface Reconstruction, and Stability of Intermediates
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Selective oxidation reactions on heterogeneous silver catalysts are essential for the mass production of numerous industrial commodity chemicals. However, the nature of active oxygen species in such reactions is still debated. To shed light on the role of different oxygen species, we studied the methanol oxidation reaction on Ag(111) single-crystal model catalyst surfaces containing two dissimilar types of oxygen (electrophilic, Oe and nucleophilic, On). X-ray photoelectron spectroscopy and low energy elect...
Selective oxidation of propylene to propylene oxide using combinatorial methodologies
Miyazaki, T; Ozturk, S; Onal, I; Senkan, S (Elsevier BV, 2003-06-30)
Direct oxidation of propylene by oxygen to propylene oxide (PO) has been studied through the application of the techniques of combinatorial catalysis. Catalytic materials containing single and binary metal components were prepared by impregnating standard gamma-Al2O3 pellets. In the first stage, 34 single component catalytic materials at three different metal loading levels were prepared and screened for PO activity and selectivity using array channel microreactors and mass spectrometry. Experiments were co...
Asymmetric synthesis of 2,3-dihydrofurans with bifunctional quinine / squaramide organocatalysts
Bozdemir, Merve; Tanyeli, Cihangir; Department of Chemistry (2019)
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-nitroviny...
Tanyeli, Cihangir (Informa UK Limited, 1989-01-01)
Some phenolic biphenyl compounds have been synthesised via the annulation reactions of 4-methoxy-2- pyrone with various active methyl 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.