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  • Title: The synthesis of a new class of chiral pincer ligands and their applications in enantioselective catalytic fluorinations and the Nozaki-Hiyama-Kishi reaction.
    Author: Deng QH, Wadepohl H, Gade LH.
    Journal: Chemistry; 2011 Dec 23; 17(52):14922-8. PubMed ID: 22052847.
    Abstract:
    A new class of chiral tridentate N-donor pincer ligands, bis(oxazolinylmethylidene)isoindolines (boxmi), was synthesized in three steps starting from readily available phthalimides. Their reaction with ethyl (triphenylphosphoranylidene)acetate by means of a key-step Wittig reaction gave the ligand backbones, which were condensed with amino alcohols and then cyclized to obtain the corresponding ligands. These ligands were subsequently applied in the nickel(II)-catalyzed enantioselective fluorination of oxindoles and β-ketoesters to obtain the corresponding products with enantioselectivities of up to >99% ee and high yields. Application of the chiral pincer ligands in the chromium-catalyzed enantioselective Nozaki-Hiyama-Kishi reaction of aldehydes gave the corresponding alcohols with an optimal enantioselectivity of 93%.
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