Palladium(0)-Catalyzed Intermolecular Asymmetric Allylic Dearomatization of Substituted β-Naphthols with Morita-Baylis-Hillman (MBH) Adducts.

Pd-catalyzed intermolecular asymmetric allylic dearomatization of substituted β-naphthol derivatives with Boc-protected Morita-Baylis-Hillman (MBH) adducts was developed. The reaction occurs smoothly in 1,4-dioxane at room temperature in the presence of [Pd(C 3 H 5 )Cl] 2 (2.5 mol %), ( S , S p )-PHOX ligand (5.5 mol %), and Li 2 CO 3 (1.0 equiv). A series of dearomatized products were afforded in moderate to excellent yields and enantioselectivity (up to 99% yield, 97% ee). Furthermore, the compatibility with gram-scale reaction and mild conditions make the current method synthetically useful.