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Cyclization-oxidation of 1,6-enyne derivatived from Baylis-Hillman adducts via Pd(II)/Pd(IV)-catalyzed reactions: stereoselective synthesis of multi-substituted bicyclo[3.1.0] hexanes and insight into reaction pathways
Authors:Hui Liu
Affiliation:Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, People’s Republic of China
Abstract:Cyclization-oxidation of Baylis-Hillman adducts provides a convenient method to stereoselectively synthesize variety of multi-substituted bicyclo[3.1.0] ring systems via Pd(II)/Pd(IV)-catalyzed reactions. We also disclose that C-Pd(IV) intermediate can undergo reductive elimination through SN2-type attack by the latent nucleophile of vinyl acetate to afford Csp3-Csp3 bond formation with inversion of configuration at the Pd(IV)-bounded carbon.
Keywords:Baylis-Hillman adduct   Bicyclo[3.1.0]   SN2-type reductive elimination   C-C bond formation   Cyclization-oxidation
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