Palladium(0)-Catalyzed Intermolecular Asymmetric Allylic Dearomatization of Substituted β-Naphthols with Morita–Baylis–Hillman (MBH) Adducts
Qingxia Zhang, Qing Gu, Shu‐Li You
Abstract
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(C3H5)Cl]2 (2.5 mol %), (S, Sp)-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.
Topics & Concepts
ChemistryAllylic rearrangementIntermolecular forceAdductCatalysisPalladiumYield (engineering)Medicinal chemistryOrganic chemistryStereochemistryMoleculeMaterials scienceMetallurgyAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality SynthesisOxidative Organic Chemistry Reactions