A Catalytic Route to Acyclic Chiral Building Blocks:Applications of the Catalytic Asymmetric Conjugate Addition of Organozinc Reagents to Cyclic Enones

Through the Cu-phosphoramidite-catalyzed asymmetric conjugate addition a number of chiral cyclic enones are available with high ee. Here we report the sequential conjugate addition to these enones as a route towards multisubstituted chiral cyclic ketones. A subsequent Baeyer-Villiger oxidation followed by ring-opening results in various linear synthons containing multiple stereocenters. This procedure represents a short, catalytic, and highly enantioselective route to a variety of acyclic chiral building blocks.