Stereoselective synthesis of N-heterocycles: application of the asymmetric Cu-catalyzed addition of Et2Zn to functionalized alkyl and aryl imines |
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Authors: | Isabelle Bonnaventure |
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Institution: | Department of Chemistry, Université de Montréal, PO Box 6128, Station Downtown, Montreal, QC H3C 3J7, Canada |
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Abstract: | The preparation of N-heterocycles from alkyl- and aryl-substituted imines is described. The key step involves a copper-catalyzed addition of diethylzinc to functionalized alkyl-substituted imines that were generated in situ from the sulfinic acid adducts. The nucleophilic addition products were then converted to 2-substituted pyrrolidines and piperidines. Aryl-substituted imines were transformed into enantioenriched 1- and 1,4-substituted tetrahydroisoquinolines. |
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Keywords: | α-Chiral amines Asymmetric catalysis Chemoselectivity Heterocycles Functionalized imines |
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