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

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 S N2-type attack by the latent nucleophile of vinyl acetate to afford C sp 3 – C sp 3 bond formation with inversion of configuration at the Pd(IV)-bounded carbon.