Heterobimetallic Zinc/Strontium Catalysis: Z/E-Selective Asymmetric Conjugate Addition of 3-Acetoxy-2-oxindoles to Alkynones

A chiral Zn–Sr heterobimetallic catalyst system generated in situ has been developed for the first highly Z/E-selective asymmetric conjugate addition of 3-acetoxy-2-oxindoles to alkynones. Both terminal alkynones and nonterminal alkynones could be applied to the heterobimetallic catalytic system. The corresponding 3-alkenyl-3-acyloxy-2-oxindoles were obtained in moderate to excellent yields (55–99%) with high E:Z ratios (8:1–30:1) and high enantioselectivities (86–99% ee).