Enantioselective aza-Henry reaction of t-Boc protected imines and nitroalkanes with bifunctional squaramide organocatalysts

2016-08-25
Susam, Zeynep Dilşad
Tanyeli, Cihangir
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https://hdl.handle.net/11511/72825
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Enantioselective aza-Henry reaction of t-boc protected imines and nitroalkanes with bifunctional squaramide organocatalysts
Susam, Dilşad; Tanyeli, Cihangir; Department of Chemistry (2015)
The first part of this thesis comprises the application of a Cinchona alkaloid derived, bifunctional squaramide organocatalyst in the aza-Henry reaction of t-Boc protected imines and nitroalkanes. The target chiral β-nitroamines are chosen because; they are quite feasible for the corresponding α-amino acids and 1,2-diamines, which are basic structural motif in many natural products and key materials of the many pharmaceuticals. In this part, 12 different chiral β-nitroamine derivatives were synthesized with...
Enantioselective aza-Henry reaction of t-Boc protected imines and nitroalkanes with bifunctional squaramide organocatalysts
Susam, Zeynep Dilşad; Tanyeli, Cihangir (2017-05-07)
An organocatalytic asymmetric aza-Henry reaction of t-Boc protected imines with nitroalkanes has been established by chiral acid-base type bifunctional Cinchona alkaloid/squaramide organocatalysts. The cooperation of a quinine motif as a base and sterically encumbered squaramide (H-bond donor) enabled mostly complete conversion of a range of reactants into the corresponding aza-Henry products at room temperature with good selectivities (up to 91% ee with 10 mol% catalyst loading).
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A series of chiral bifunctional quinine and 2-aminoDMAP based squaramide organocatalysts are evaluated in Friedel-Crafts alkylation of indoles with nitroolefins. These 3-substituted indole derivatives are synthesized in the presence of sterically encumbered tert-butyl squaramide/quinine with high enantioselectivity (up to >99% ee) and moderate chemical yields (up to 80%) by representing as chiral precursors for very important biologically active molecules. Besides, this asymmetric transformation provides a ...
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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 ...
Enantioselective decarboxylative michael and aldol reactions with bifunctional squaramide organocatalysts
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The decarboxylative Michael and aldol reactions are quite new in the asymmetric studies and are used for forming new C-C bonds by nucleophilic attack. In the first part of this thesis, decarboxylative Michael reaction of isatylidene malononitriles with ethyl benzoyl acetate was accomplished in the presence of chiral 2- aminoDMAP and quinine derived bifunctional acid/base organocatalysts, which are developed in our research group. In this part, 12 derivatives were synthesized with quinine based 1-adamantyl s...
Citation Formats
Z. D. Susam and C. Tanyeli, “Enantioselective aza-Henry reaction of t-Boc protected imines and nitroalkanes with bifunctional squaramide organocatalysts,” 2016, Accessed: 00, 2021. [Online]. Available: https://hdl.handle.net/11511/72825.
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