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Updated: Dec 11, 2025
Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Allylsilane Reagent-Controlled Divergent Asymmetric Catalytic Reactions of 2-Naphthoquinone-1-methide
Xiangfeng Lin1,2, Yan Liu1, Can Li1
1State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China.
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 ScIII /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.
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