Asymmetric synthesis of 3,4-dihydroxyglutamic acids via enantioselective reduction of cyclic meso-imide |
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Authors: | Makoto Oba Shinichi Koguchi |
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Institution: | Department of Material Science and Technology, Tokai University, 317 Nishino, Numazu, Shizuoka 410-0395, Japan |
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Abstract: | Stereoselective synthesis of (3S,4S)- and (3R,4R)-series of 3,4-dihydroxyglutamic acids was investigated. The key reaction in this synthesis is asymmetric reduction of meso-imide derived from meso-tartaric acid. Lewis acid-promoted cyanation of the obtained optically active lactam via the acyliminium intermediate followed by standard deprotection procedure afforded the desired 3,4-dihydroxyglutamic acids. |
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Keywords: | Asymmetric synthesis 3 4-Dihydroxyglutamic acid meso-Imide Desymmetrization |
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