Carbohydrate derived bicyclic azetidin-3-ones as scaffolds for highly functionalized azetidines |
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| Affiliation: | 1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation;2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation;1. School of Environmental Sciences, University of Liverpool, UK;2. Water Resources Unit, Institute for Environment and Sustainability, Joint Research Centre, European Commission, Italy;3. Institute for Water Resources (IWR), US Army Corps of Engineers (USACE), USA;4. International Centre for Integrated Water Resources Management (ICIWaRM) u/a UNESCO, USA;5. National Research Institute of Science and Technology for Environment and Agriculture (Irstea), France;6. ILTER Science and Programs Committee, Institute of Arctic and Alpine Research, University of Colorado Boulder, USA;7. Federal Institute of Hydrology in Koblenz, Germany;8. Division of Water Sciences, International Hydrological Programme (IHP), UNESCO, France;9. Department of Microbial Ecology, Faculty of Biology, University of Warsaw, Poland;10. Department of Hydrology, University of Warsaw, Poland;11. Faculty of Architecture and Town Planning, Technion, Israel Institute of Technology, Israel;12. Chartered Institution of Water and Environmental Management (CIWEM), Rivers & Coastal Group, UK;13. UNESCO Polish Committee, Poland;14. Research Institute for Water Security (RIWS), Wuhan University, China;15. Chinese Academy of Sciences, China;p. European Regional Centre for Ecohydrology of Polish Academy of Sciences u/a UNESCO, Poland;q. Department of Applied Ecology, University of Łódź, Poland |
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| Abstract: | Bicyclic azetidin-3-ones with no acidic α-hydrogens, prepared in good yields via cis-2,4-di-O-triflates of pyranosides, are stable divergent intermediates for the synthesis of highly substituted azetidines, as illustrated by the synthesis of (2R,3R,4R)-3-hydroxy-4-(hydroxymethyl)-3-methylazetidine-2-carboxylic acids. Preliminary studies on the reactions of bicyclic azetidinones indicate their potential as scaffolds for novel complex azetidines. |
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