Catalytic Enantioselective 1,4-Iodofunctionalizations of Conjugated Dienes

Abstract

The first catalytic enantioselective 1,4-iodofunctionalizations of conjugated dienes have been developed. Starting from β,γ,δ,ε-unsaturated oximes and 4-Ns hydrazones, these N-iodosuccinimide-mediated reactions are catalyzed by newly modified tertiary aminothiourea derivatives and furnish Δ(2)-isoxazoline and Δ(2)-pyrazoline derivatives, respectively, containing an (E)-allyl iodide group at the quaternary stereogenic center generally in high yield and with excellent enantioselectivity (up to 98.5:1.5 er).