Transmetallation of n-(trialkylstannyl)methylimines. A new method for the generation and cycloaddition of 2-azaallyl anions. |
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| Institution: | 1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation;2. Ionic Liquid Research Laboratory, Merck KGaA, 64293 Darmstadt, Germany;1. Department of Chemistry, Josip Juraj Strossmayer University of Osijek, Cara Hadrijana 8/A, 31000 Osijek, Croatia;2. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-481 Warsaw, Poland;3. University of Zagreb, Faculty of Science, Department of Chemistry, Division of General and Inorganic Chemistry, Horvatovac 102a, 10000 Zagreb, Croatia;1. Laboratoire de Synthèse, Réactivité Organiques et Catalyse, Institut de Chimie, UMR 7177 - CNRS, Université de Strasbourg, 4 rue Blaise Pascal, 67070 Strasbourg, France;2. Institut des Molécules et Matériaux du Mans, Université du Maine, Avenue Olivier Messiaen, 72085 Le Mans, France |
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| Abstract: | Transmetallation of imines 1 at −78° with RLi provided 2-azaallyl anions 2, which readily undergo cycloaddition with olefinic anionophiles, providing pyrrolidines. Of particular note is the generation of unstabilized 2-azaallyl anions for the first time (Table 1, entries 1–3). |
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