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Asymmetric synthesis of (2S,3R,4R)-ethoxycarbonylcyclopropyl phosphonoglycine
Institution:1. UMR 5810 Laboratoire des Aminoacides Peptides et Protéines, Université Montpellier I et II, Place E. Bataillon, 34095 Montpellier Cédex, France;2. UPR 2301, Institut de Chimie des Substances Naturelles, 91198 Gif sur Yvette, France;3. Faculté des Sciences Saiss, BP 2022 Fes, Maroc;1. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of Russian Academy of Sciences, Arbuzov St., 8, Kazan 420088, Russia;2. Department of Pharmaceutical Terchnology, Faculty of Pharmacy, University of Coimbra (FFUC), Pólo das Ciências da Saúde, Azinhaga de Santa Comba, 3000-548 Coimbra, Portugal;3. CEB - Centre of Biological Engineering, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal;1. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Arbuzov St., 8, Kazan, 420088, Russia;2. Kazan Federal University, Kremlyovskaya St., 18, Kazan, 420008, Russia;3. Kazan National Research Technological University, Karl Marx St., 68, 420015, Kazan, Russia;4. Institute for Solid State Physics and Optics, Wigner Research Centre for Physics, Hungarian Academy of Sciences, Budapest, Hungary;5. Department of Pharmaceutical Technology, Faculty of Pharmacy, University of Coimbra, Coimbra, Portugal;6. REQUIMTE/LAQV, Group of Pharmaceutical Technology, Faculty of Pharmacy, University of Coimbra, Coimbra, Portugal
Abstract:The synthesis of enantiomerically pure (2S,3R,4R)-ethoxycarbonylcyclopropyl phosphonoglycine is described, the key-step involving 1,4-addition of a chiral enolate to ethyl 4-bromo-crotonate.
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