Stereoselective synthesis of 3,4-disubstituted pyroglutamates by ring transformation of 5-ylidene-1,3-dioxan-4-ones with N-(diphenylmethylene)-glycinate |
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| Institution: | 1. Institut für Chemie, Humboldt-Universität Berlin, Hessische Straße 1–2, D-10115 Berlin, Germany;2. HEJ Research Institute of Chemistry, University of Karachi, Karachi 75270, Pakistan;1. Department of Breast and Endocrine Surgery, Haukeland University Hospital, Bergen, Norway;2. Research Department, Stavanger University Hospital, Stavanger, Norway;3. Department of Mathematics and Natural Science, University of Stavanger, Stavanger, Norway;4. Department of Sport and Physical Activity, Bergen University College, Bergen, Norway;5. Uni Research Health, Bergen, Norway;6. Department of Surgery, Stavanger University Hospital, Stavanger, Norway;7. Department of Clinical Science, University of Bergen, Bergen, Norway;8. Department of Medicine, Haukeland University Hospital, Bergen, Norway;9. Department of Clinical Medicine, University of Bergen, Bergen, Norway;1. Université de Lyon, Institut des Sciences Analytiques, UMR 5280 CNRS, Université Claude Bernard Lyon 1, 5 rue de la Doua, 69100 Villeurbanne, France;2. ARNA laboratory, Inserm U1212, CNRS UMR 5320, Université de Bordeaux, 146 rue Léo Saignat, 33076 Bordeaux Cedex, France;1. School of Pharmaceutical Sciences, Institute of Drug Discovery and Development, Key Laboratory of Advanced Pharmaceutical Technology, Ministry of Education of China, Zhengzhou University, Zhengzhou 450001, PR China;2. Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, Zhengzhou 450001, PR China;1. Departamento de Química Orgánica, Facultad de Ciencias Químicas, University of Salamanca, Salamanca, 37008, Spain;2. Servicio de Difracción de Rayos X, Universidad de Salamanca, Salamanca, 37008, Spain;3. Departamento de Química Física, Facultad de Ciencias Químicas, University of Salamanca, Salamanca, 37008, Spain;1. Key Laboratory of Resource Biology and Biotechnology in Western China, Ministry of Education, The College of Life Sciences, Northwest University, Xi''an, 710069, PR China;2. Department of Medicinal Chemistry, School of Pharmacy, Fourth Military Medical University, Xi''an, 710032, PR China;3. Department of Pharmacy, Fuzong Clinical Medical College of Fujian Medical University (900 Hospital of the Joint Logistics Team), Fuzhou, 350025, PR China |
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| Abstract: | N-(Diphenylmethylene)-glycinate gives stereoselective conjugate addition to readily available (E) and (Z)-5-ylidene-1,3-dioxan-4-ones. Hydrolytic cleavage of the imine functionality of the resulting Michael-adducts causes ring transformation to new, optically active 3,4-disubstituted pyroglutamates. |
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