Diastereoselective Synthesis of Highly Functionalized Proline Derivatives |
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| Authors: | Anna N. Philippova Daria V. Vorobyeva Pavel S. Gribanov Fedor M. Dolgushin Sergey N. Osipov |
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| Affiliation: | 1.A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28/1, 119334 Moscow, Russia;2.N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky Prosp., 119071 Moscow, Russia;3.Plekhanov Russian University of Economics, 36 Stremyanny per., 117997 Moscow, Russia |
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| Abstract: | An efficient way to access highly functionalized proline derivatives was developed based on a Cu(I)-catalyzed reaction between CF3-substituted allenynes and tosylazide, which involved a cascade of [3 + 2]-cycloaddition/ketenimine and a rearrangement/Alder-ene cyclization to afford the new proline framework with a high diastereoselectivity. |
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| Keywords: | 1,6-allenynes cycloaddition alder-ene reaction catalysis prolines 1,2,3-triazoles |
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