Stereoselective synthesis of (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid via C-H insertion of alkylidenecarbene |
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| Authors: | Ohira Susumu Akiyama Megumi Kamihara Kumiko Isoda Yuichi Kuboki Atsuhito |
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| Institution: | Department of Biological Chemistry, Faculty of Science, Okayama University of Science, Japan. sohira@dbc.ous.ac.jp |
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| Abstract: | (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic acid (ACPD), a potent agonist of metabotropic glutamate receptors, was synthesized from L-serine. The chiral quaternary center was constructed by C-H insertion of the alkylidenecarbene, this being generated by the reaction between lithiotrimethylsilyldiazomethane and the corresponding ketone. |
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