A facile method for synthesis of (R)-(−)- and (S)-(+)-homocitric acid lactones and related α-hydroxy dicarboxylic acids from d- or l-malic acid |
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| Authors: | Peng-Fei Xu Tsuyoshi Matsumoto Kazuyuki Tatsumi |
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| Affiliation: | a Research Center for Materials Science and Department of Chemistry, Graduate School of Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8602, Japan
b State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, PR China |
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| Abstract: | We report here a simple and convenient route for the stereoselective synthesis of (R)-(−)- and (S)-(+)-homocitric acid lactones, which play very important roles in biochemistry. The method involves only three steps, starting from the readily available methyl 3-iodopropionate and d-malic acid or l-malic acid, respectively. The stereoconfiguration of the target molecules has been achieved via a self-regeneration approach with over 98% diastereoselectivity and significantly improved yield over the previous methods. |
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| Keywords: | Homocitric acid lactones α-Hydroxy dicarboxylic acids Nitrogenase |
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