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  • Title: Enantioselective Synthesis of Isoxazolines Enabled by Palladium-Catalyzed Carboetherification of Alkenyl Oximes.
    Author: Wang L, Zhang K, Wang Y, Li W, Chen M, Zhang J.
    Journal: Angew Chem Int Ed Engl; 2020 Mar 09; 59(11):4421-4427. PubMed ID: 31868991.
    Abstract:
    Reported here is a highly efficient Pd/Xiang-Phos catalyzed enantioselective carboetherification of alkenyl oximes with either aryl or alkenyl halides, delivering various chiral 3,5-disubstituted and 3,5,5-trisubstituted isoxazolines in good yields with up to 97 % ee. The sterically bulky and electron-rich (S,Rs)-NMe-X2 ligand is responsible for the excellent reactivities and enantioselectivities. The salient features of this transformation include mild reaction conditions, general substrate scope, good functional-group tolerance, good yields, high enantioselectivities, easy scale-up, and application in the late-stage modification of bioactive compounds. The obtained products can be readily transformed into useful chiral 1,3-aminoalcohols.
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