Allylsilane Reagent‐Controlled Divergent Asymmetric Catalytic Reactions of 2‐Naphthoquinone‐1‐methide
Xiangfeng Lin, Yan Liu, Can Li
Abstract
Abstract Herein, the first allylsilane reagent‐controlled divergent asymmetric Hosomi–Sakurai conjugate allylation and hetero‐Diels–Alder (HDA) with 2‐naphthoquinone‐1‐methide (2‐Nap‐Q‐1‐M) under the catalysis of Sc III /Feng ligand complex is reported. With these methods, a variety of uniquely substituted chiral allyl‐functionalized diaryl compounds and naphthopyran products were obtained in a straightforward and highly stereoselective (up to 96.5:3.5 e.r.) manner under mild conditions. Moreover, it is demonstrated that 2‐Nap‐Q‐1‐M can serve as an efficient diene for a side asymmetric Diels–Alder (D‐A) reaction. This principle can provide a straightforward access to hydrophenalene in an optically active form, which represents a structural core of various natural products and bioactive molecules.