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Tunable Palladium-Catalyzed [2π + 2σ] Cycloaddition/Alder-Ene Reactions of Vinylbicyclo[1.1.0]butanes with Cyclic
Lan Zheng1, Chenxiang Lin1, Liu Yang1
1Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning530001, China.
Abstract:
A condition-controlled regiodivergent [2π + 2σ] cycloaddition/Alder-ene reaction of vinylbicyclo[1.1.0]butanes with cyclic N-sulfonylimines enabled by palladium catalysis is described. This protocol provides a wide range of azabicyclo[2.1.1]hexanes (aza-BCHs) in 30-71% yields with good to excellent selectivities. Additionally, cyclobutenes bearing two quaternary stereocenters are conveniently generated in good yields with excellent selectivities via a palladium-catalyzed Alder-ene reaction. This strategy features mild reaction conditions, a broad substrate scope, and excellent selectivities. Furthermore, scale-up reaction and derivatizations of the resulting aza-BCHs further demonstrate the practical utility of this protocol.
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