Copper-catalyzed enantioselective carbonylation toward α-chiral secondary amides |
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Authors: | Yang Yuan Fengqian Zhao Xiao-Feng Wu |
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Institution: | Leibniz-Institut für Katalyse e.V., Albert-Einstein-Straße 29a, 18059 Rostock Germany.; Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 116023 Dalian Liaoning China, |
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Abstract: | Secondary amides are omnipresent structural motifs in peptides, natural products, pharmaceuticals, and agrochemicals. The copper-catalyzed enantioselective hydroaminocarbonylation of alkenes described in this study provides a direct and practical approach for the construction of α-chiral secondary amides. An electrophilic amine transfer reagent possessing a 4-(dimethylamino)benzoate group was the key to the success. This method also features broad functional group tolerance and proceeds under very mild conditions, affording a set of α-chiral secondary amides in high yields (up to 96% yield) with unprecedented levels of enantioselectivity (up to >99% ee). α,β-Unsaturated secondary amides can also be produced though the method by using alkynes as the substrate.A copper-catalyzed regioselective and enantioselective intermolecular hydroaminocarbonylation of alkenes with electrophilic hydroxylamines has been developed. |
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