Asymmetric synthesis of 5-substituted pyrrolidinones via a chiral N-acyliminium equivalent |
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| Affiliation: | 1. Institut de Chimie des Substances Naturelles, CNRS, 1 avenue de la Terrasse, F-91198 Gif-sur-Yvette, France;2. Laboratoire de Chimie Thérapeutique, UMR 8638 associée au CNRS et à l''Université René Descartes, Faculté de Pharmacie, 4 avenue de l''Observatoire, 75270 Paris cedex, France;1. Departamento de Química Orgánica, Facultad de Ciencias, Campus Universitario Puerto Real, Universidad de Cádiz, Puerto Real, Cádiz 11510, Spain;2. Department of Chemistry, University of Reading, Whiteknights, Reading RG6 6AD, United Kingdom;1. College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, People’s Republic of China;2. College of Science, Nanjing Forestry University, Nanjing 210037, People’s Republic of China;3. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore;1. Département de Chimie, Université de Montréal, C.P. 6128, Succursale Centre-Ville, Montréal, Québec H3C 3J7, Canada;2. Inorganic Chemistry I – Bioinorganic Chemistry, Ruhr-University Bochum, Universitätsstrasse 150, 44801 Bochum, Germany;3. INRS – Institut Armand-Frappier, Groupe de Recherche en Ingénierie des Peptides et en Pharmacothérapie (GRIPP), Université du Québec, Ville de Laval, Québec H7V 1B7, Canada;1. Faculty of Pharmacy, Yasuda Women’s University, 6-13-1, Yasuhigashi, Asaminami-ku, Hiroshima 731-0153, Japan;2. Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan;3. Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan |
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| Abstract: | 5-Substituted pyrrolidinones 5 were synthesized in good yields and with fair to good diastereoselectivities from the chiral non-racemic oxazolopyrrolidinone 4. Various nucleophiles including cuprates, silanes and phosphites were used. The chiral induction is thought to arise from a chelated N-acyliminium species. |
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