Copper-catalyzed conjugate addition of allene-derived nucleophiles to alkenyl-substituted carboxamides

CHINESE CHEMICAL LETTERS(2024)

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摘要
Catalytic Michael addition reaction represents a fundamental importance in organic synthetic chem-istry. Whereas corresponding conversions toward intrinsically low reactive enamide remains an ongoing challenging. We herein report a copper-catalyzed conjugate addition of allenes to ,B-substituted alkenyl amides, one of the most challenging Michael acceptors. The present method utilizes readily available al-lenes as the latent carbon-based nucleophiles and simple, common ,B-substituted alkenyl amides as start-ing materials, unlike previous methods that usually preinstall an activating group to improve the reac-tivity of amide or uses highly reactive stoichiometric quantities of organometallics. Hence, this approach shows good functional group compatibility and can be implemented under mild reaction conditions with excellent level of chemo-and regioselectivities. (c) 2023 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
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关键词
CuH catalysis,Allenes,Unsaturated amide,Conjugate addition,Regioselectivity
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