General and practical catalytic enantioselective Strecker reaction of ketoimines: significant improvement through catalyst tuning by protic additives |
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| Authors: | Nobuki Kato Masato Suzuki Masakatsu Shibasaki |
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| Institution: | a Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
b PRESTO, Japan Science and Technology Corporation, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan |
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| Abstract: | Significant improvement in enantioselectivity and catalyst activity was achieved for the catalytic enantioselective Strecker reaction. Using a catalyst (1-2.5 mol %) prepared from Gd(OiPr)3 and d-glucose derived ligand 1, and in the presence of 2,6-dimethylphenol as an additive, high enantioselectivity was obtained from a wide range of ketoimines, including heteroaromatic and cyclic ketoimines. The new method was applied to an efficient catalytic asymmetric synthesis of sorbinil, a therapeutic agent for diabetic complications. |
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| Keywords: | Asymmetric catalysis Strecker reaction Ketoimines Disubstituted amino acids Additive effect |
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