- Necmettin Erbakan Üniversitesi Fen ve Mühendislik Bilimleri Dergisi
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- Chiral Diazadioxocalix[2]arene[2]triazine-Based Derivative as Organocatalyst for Enantioselective Mi...
Chiral Diazadioxocalix[2]arene[2]triazine-Based Derivative as Organocatalyst for Enantioselective Michael Reaction of Nitrostyrenes with Anthrone
Authors : Ummu Ozgun, Hayriye Nevin Genç, Abdulkadir Sırıt
Pages : 58-68
Doi:10.47112/neufmbd.2024.32
View : 44 | Download : 45
Publication Date : 2024-04-30
Article Type : Research
Abstract :Asymmetric synthesis, also known as chiral, enantioselective or stereoselective synthesis, is an organic synthesis which allows the formation of chiral compounds containing one or more stereogenic centers. Since different enantiomers of a molecule usually show different biological activity from each other, asymmetric synthesis is a very important topic in the pharmaceutical industry and organic chemistry. One of the most preferred methods to obtain a chiral compound from non-chiral compounds is the use of chiral catalysts. In this study, a chiral catalyst, which is not available in the literature, was synthesized for use in the asymmetric Michael reaction using anthrone and different nitrostyrene derivatives. First, diazadioxocalix[2]arene[2]triazine, which is available in the literature, was synthesized as the starting material of the chiral catalyst. (S)-(+)-1-cyclohexylethylamine was reacted with the synthesized starting material to obtain the substance to be used as a chiral catalyst in the enantioselective reaction. During the study, all reactions were monitored by thin layer chromatography and the obtained substances were purified by column chromatography. The structures of the purified products were elucidated by FTIR, 1H NMR and 13C NMR techniques and optical rotation angles were measured. The synthesized catalyst was tested in asymmetric Michael reaction and high yields and high enantioselectivity were obtained (95% yield and 98% ee).Keywords : Organokataliz, Asimetrik sentez, Michael reaksiyonu