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    Öğe
    A Novel Methodology for the Asymmetric Synthesis of 2,3,5-Trisubstituted Piperazine Derivatives
    (Georg Thieme Verlag Kg, 2024) Beksultanova, Nurzhan; Özdemir, Özge; Polat Çakır, Sıdıka; Aygün, Muhittin; Doğan, Özdemir
    Piperazines constitute an important structural feature of many pharmaceuticals. For the discovery of new drugs, the ability to modify the lead compound's structure is crucial. Herein, we provide an efficient method for the synthesis of chiral 2,3,5-trisubstituted piperazine structures. Our route enables the synthesis of several novel chiral aryl aziridinyl ketones that could be converted into aziridine-fused bicyclic imines. The reduction of these imines and the nucleophilic ring-opening reaction of the aziridine ring allowed us to synthesize highly functionalized piperazine derivatives.
  • Küçük Resim
    Öğe
    FAM-Ag-catalyzed asymmetric synthesis of heteroaryl-substituted pyrrolidines
    (Wiley, 2021) Beksultanova, Nurzhan; Gözükara, Zeynep; Araz, Mihrimah; Bulut, Merve; Polat-Çakır, Sıdıka; Aygün, Muhittin; Doğan, Özdemir
    New derivatives of FAM (ferrocenyl aziridinyl methanol) ligands NFAM1–4 (naphthyl ferrocenyl aziridinyl methanol) and CFAM1–4 (cyclohexyl ferrocenyl aziridinyl methanol) were synthesized to form a small ligand library and used as chiral catalysts with AgOAc for the asymmetric synthesis of heteroaryl-substituted pyrrolidines by the 1,3-dipolar cycloaddition (1,3-DC) reaction of azomethine ylides. 2-Thienyl, 2-furyl, 2-, 3-, and 4-pyridyl aldimines were prepared and used with N-methylmaleimide, dimethyl maleate, tert-butyl acrylate, methyl acrylate, and acrylonitrile to form the corresponding heteroaryl-substituted pyrrolidines. 1,3-DC reactions yielded the expected cycloadducts in up to 89% yield and up to 76% ee that could be increased up to 95% ee upon crystallization. New chiral ligands NFAM1–4 and CFAM1–4 were fully characterized, and their absolute stereochemistry was determined by single-crystal X-ray analysis.