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
Karatok, Mustafa; Şensoy, Mehmet Gökhan; Vovk, Evgeny I.; Toffoli, Hande; Toffoli, Daniele; Ozensoy, Emrah (2021-01-01)
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...
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.
PFAM catalyzed enantioselective diethylzinc addition to imines
Doğan, Özdemir (2015-01-01)
Chiral amines are important starting materials for the synthesis of biologically important compounds. Enantioselective addition of dialkylzinc reagents to imines is a reliable method for the synthesis of these compounds. Different chiral catalysts were developed and used for this method. Phosphorous based PFAM catalysts were tried for the first time in the enantioselective synthesis of amines by reacting diethylzinc with N-sulfonyl imines and N-diphenylphosphinoyl imines. Chiral amines were isolated with mo...
Facile synthesis of (4-nitrophenyl)thio-substituted 1- pyrrolines
Korkmaz, Esra; Zora, Metin; Department of Chemistry (2019)
The importance of heterocyclic compounds is enormous in synthetic organic chemistry due to their presence in bioactive molecules. Five-membered 1-pyrrolines are one of the most important classes of them. They have recently drawn great attention from synthetic chemists since they have a prominent role for the synthesis of a great number of pharmaceutical molecules. Therefore, there is intense research on their synthesis. In this project, we concentrated on the synthesis of (4-nitrophenyl)thio-substituted 1- ...
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.