Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from d-ribose |
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| Affiliation: | 1. Department of Civil Engineering, University of Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano (SA), Italy;2. Plataforma Solar de Almería–CIEMAT, Carretera Senés km 4, 04200 Tabernas (Almería), Spain;1. School of Basic Sciences (SB), Institute of Chemical Science and Engineering (ISIC), Group of Advanced Oxidation Processes (GPAO), École Polytechnique Fédérale de Lausanne (EPFL), Station 6, CH-1015 Lausanne, Switzerland;2. School of Architecture, Civil and Environmental Engineering (ENAC), Environmental Engineering Institute (IIE), Laboratory for Water Quality and Treatment (LTQE), École Polytechnique Fédérale de Lausanne (EPFL), Station 2, CH-1015 Lausanne, Switzerland;1. Grupo de Investigación en Remediación Ambiental y Biocatálisis (GIRAB), Instituto de Química, Facultad de Ciencias Exactas y Naturales, Universidad de Antioquia UdeA, Calle 70 No. 52-21, Medellín, Colombia;2. Grupo de Diseño y Formulación de Medicamentos, Cosméticos y Afines (DYFOMECO), Facultad de Química Farmacéutica, Universidad de Antioquia UdeA, Calle 70 No. 52-21, Medellín, Colombia;1. School of Ecology and Environment, Inner Mongolia University, University W. Road, 010021, Huhhot, Inner Mongolia, PR China;2. School of Basic Sciences (SB), Institute of Chemical Science and Engineering (ISIC), Group of Advanced Oxidation Processes (GPAO), École Polytechnique Fédérale de Lausanne (EPFL), Station 6, CH-1015, Lausanne, Switzerland;3. College of Environment, Zhejiang University of Technology, Hangzhou, 310032, China;4. Universidad Politécnica de Madrid (UPM), E.T.S. Ingenieros de Caminos, Canales y Puertos, Departamento de Ingeniería Civil: Hidráulica, Energía y Medio Ambiente, Unidad docente Ingeniería Sanitaria, c/ Profesor Aranguren, s/n, ES-28040, Madrid, Spain |
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| Abstract: | A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of ω-oxo enoates from d-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. |
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