Pd(II)-Catalyzed Asymmetric C–H Functionalization/Dearomatization of Naphthols through Axial-to-Central Chirality Transfer

Abstract

All-carbon chiral spirocycles are highly sought-after structural motifs found in various biological drugs, natural products, chiral ligands, and catalysts. However, their catalytic asymmetric synthesis remains a significant challenge due to steric hindrance and ring strain. Herein, we present the efficient synthesis of all-carbon chiral spirocycles through a Pd(II)-catalyzed asymmetric C–H functionalization/dearomatization reaction of naphthols, utilizing an axial-to-central chirality transfer strategy. This mild and versatile protocol accommodates a broad range of functionalized naphthols and alkynes, achieving good yields and enantioselectivities (up to 93% yield and 96% ee). Additionally, the practical application of this method is illustrated through the investigation of the photophysical properties of the resulting spirocycles, highlighting their potential as host materials for organic light-emitting diodes.