Enantioselective synthesis of 2 aziridinyl phosphonates and studies of their biological activities

Doğan, Özdemir
Beksultanova, Nurzhan
Altanlar, Nurten
Şimşek, Duygu
251st ACS National Meeting (13 - 17 Mart 2016)


Enantioselective synthesis of new chiral 2-aziridinyl phosphonates and studies of their biological activities
Doğan, Özdemir; Beksultanova, Nurzhan; ALTANLAR, NURTEN; Simsek, Duygu; KARABIYIK, HASAN (2017-02-15)
A new series of chiral aziridinyl phosphonates has been synthesized and evaluated for antibacterial and antifungal activities. For the synthesis, a Gabriel-Cromwell reaction was used to form aziridinyl phosphonates in 52-83% yield. In order to evaluate antibacterial and antifungal activities, MIC values were measured. Although most of the compounds showed insignificant activity, two of them provided low to moderate antifungal activity.
Enantioselective decarboxylative michael and aldol reactions with bifunctional squaramide organocatalysts
Bayer, Ezgi; Tanyeli, Cihangir; Department of Chemistry (2018)
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...
Enantioselective synthesis of 2-(2-arylcyclopropyl)glycines: Conformationally restricted homophenylalanine analogs
Demir, Ayhan Sıtkı; Sesenoglu, O; Ulku, D; Arici, C (Wiley, 2004-01-01)
Starting from simple aromatic aldehydes and acetylfuran, (E)-1-(furan-2-yl)-3-arylprop-2-en-1-ones (2) were synthesized in high yields. Cyclopropanation of the C=C bond with trimethylsulfoxonium iodide (Me3SO+I-) furnished (furan-2-yl)(2-arylcyclopropyl)methanones 3 in 90-97% yields. Selective conversion of cyclopropyl ketones to their (E)- and (Z)-oxime ethers 5 and oxazaborolidine-catalyzed stercoselective reduction of the C-N bond followed by separation of the formed diastereoisomers, furnished (2-arylcy...
Enantioselective michael addition of 1-nitropropane to nitroolefins with 2-aminodmap and quinine based bifunctional organocatalysts
Kanberoğlu, Esra; Tanyeli, Cihangir; Department of Chemistry (2015)
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 formal synthesis of pregabalin with bifunctional acid/base organocatalysts
Kapucu, Merve; Tanyeli, Cihangir; Department of Chemistry (2013)
Pregabalin, which is marketed under the brand name of Lyrica by Pfizer, is an important chiral drug in the treatment of epilepsy and neuropathic pain. Since only S-Pregabalin is active for the treatment, asymmetric synthesis was accomplished in 6 steps and the chiral induction was done by transition metal catalysis in industrial production. In this thesis, we applied an alternative synthetic route taken place in 3 steps. The key step comprised the chiral induction done by organocatalysis and the formal asym...
Citation Formats
Ö. Doğan, N. Beksultanova, N. Altanlar, and D. Şimşek, “Enantioselective synthesis of 2 aziridinyl phosphonates and studies of their biological activities,” presented at the 251st ACS National Meeting (13 - 17 Mart 2016), San Diego, CA, USA, 2016, Accessed: 00, 2021. [Online]. Available: https://hdl.handle.net/11511/73400.