Asymmetric Allylation/Retro-Claisen Cascade Reaction of 1,3-Diketones and 1-Hydroxyallylphenols/Aniline Catalyzed by an Iridium Complex.

An asymmetric allylation/retro-Claisen cascade reaction of 1-hydroxyallylphenols/aniline with 1,3-diarylketones has been developed, and a series of chiral γ,δ-unsaturated 1,3-diaryl ketones could be produced in good to excellent yields (up to 87%) with outstanding enantioselectivities (up to 99% ee), thus providing convenient access to the synthesis of (-)-sugiresinol and calyxolane A analogues. Transformations of these chiral γ,δ-unsaturated 1,3-diaryl ketones into other derivatives have also been explored.