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  • Title: Palladium/PC-Phos-Catalyzed Asymmetric Heck/Tsuji-Trost Reactions of Amino-Tethered 1,3-Cyclohexadiene with Aryl and Alkenyl Halides.
    Author: Feng J, Shi J, Wei L, Liu M, Li Z, Xiao Y, Zhang J.
    Journal: Angew Chem Int Ed Engl; 2023 Jan 02; 62(1):e202215407. PubMed ID: 36317934.
    Abstract:
    Chiral perhydroindoles are found in a number of natural products and biologically active compounds. Therefore, the development of new asymmetric methodology for rapid access to this core is of high importance. Herein, we reported a highly regio- and diastereo-selective palladium/PC-Phos-catalyzed asymmetric Heck/Tsuji-Trost reactions of readily available amino tethered 1,3-cyclohexadienes with aryl and alkenyl halides, delivering various functionalized chiral hexahydroindoles in good yields with high enantioselectivity. The application of this reaction to the concise synthesis of (-)-α-Lycorane was demonstrated. DFT computation results indicate that the difference in ΔEdis of two migration insertion transition states determines the enantioselectivity of the reaction.
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