Biomimetic reductive amination under the continuous-flow reaction conditions |
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Authors: | Vadim A Soloshonok Hector T Catt Taizo Ono |
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Institution: | a Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of the Ukraine, Murmanska Street, Kyiv 94 02660, Ukraine b National Institute of Advanced Industrial Science and Technology (AIST), 2266 Anagahora, Shimoshidami, Moriyama-ku, Nagoya, Aichi 463-8560, Japan c Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, United States |
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Abstract: | This study present a full account of continuous-flow reaction conditions for biomimetic reductive amination of fluorinated carbonyl compounds to corresponding amines and amino acids of biomedical importance. We demonstrate that simple silica-adsorbed DBU can be used as efficient catalysts for on-column 1,3-proton shift reaction, a key transformation in the biomimetic reductive amination process. This new on-column process features operationally convenient conditions, higher chemical yields, enantioselectivity and purity of the corresponding products as compared with traditional in-flask reactions. Moreover the removal of base-catalyst, the most delicate problem of the in-flask reactions, is not an issue in the on-column process, as the silica-adsorbed DBU or polymer-bound guanidine remains on the column and can be reused. This feature renders the overall process substantially more economical and synthetically efficient, in particular, for large-scale synthesis of the corresponding fluorinated amines and amino acids target. |
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Keywords: | Transamination 1 3-Proton shift reaction On-column reactions Continuous-flow reactions Biomimetic reductive amination Fluorine-containing amines and amino acids Operationally convenient conditions Asymmetric synthesis |
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