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    N-Boc-Amino Acid Mediated Morita-Baylis Hillman reaction of methylphenyl glyoxylate
    (2023) Koz, Gamze; Coskun, Necdet
    The organocatalyzed Morita-Baylis Hillman (MBH) reaction of ?-keto esters is a challenging carbon-carbon bond-forming reaction. We developed a catalytic system for the MBH reaction of methylphenyl glyoxylate with methyl vinyl ketone in a polar aprotic solvent. We used N-Boc-L-pipecolinic acid as a proton transfer mediator and 4-dimethylaminopyridine as the tertiary amine catalyst. We obtained the MBH adduct with a 66% yield in 48h. We proposed a detailed reaction mechanism involving a transition state that includes the hydrogen transfer by the acid functional group of N-Boc-L-pipecolinic acid.
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    (Taylor & Francis Inc, 2016) Koz, Gamze; Koz, Ömer; Coskun, Necdet
    A series of medicinally important 2-amino-4-(nitromethyl)-4H-chromene-3-carbonitriles were synthesized using enantioselective conjugate addition of nitromethane to 2-iminochromenes. The reactions were performed using L8-Cu (II) catalytic system and moderate to good enantioselectivities (62-88%) and yields (66-96%) were obtained.