Pd-Catalyzed intermolecular asymmetric allylic dearomatization of 1-nitro-2-naphthols with MBH adducts

Abstract

An asymmetric allylic dearomatization reaction of 1-nitro-2-naphthol derivatives with Morita–Baylis–Hillman (MBH) adducts has been developed. By utilizing Pd catalyst derived from Pd(OAc)₂ and Trost ligand (R,R)-L1, the reaction proceeded smoothly in 1,4-dioxane at room temperature, affording substituted β-naphthalenones in good yields (up to 92%) and enantioselectivity (up to 90% ee). A range of substituted 1-nitro-2-naphthols and MBH adducts were found to be compatible under the optimized conditions. This reaction provides a convenient method for the synthesis of enantioenriched 1-nitro-β-naphthalenone derivatives.