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

Pd-catalyzed intermolecular asymmetric allylic dearomatization of substituted beta-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(C3H5)Cl](2) (2.5 mol %), (S, S-p)-PHOX ligand (5.5 mol %), and Li2CO3 (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.

Automated summary

The Pd-catalyzed intermolecular asymmetric allylic dearomatization reaction has been developed, showing moderate to excellent yields and enantioselectivity. The compatibility with gram-scale reactions and mild conditions make this method synthetically useful.