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  • Title: Catalytic asymmetric synthesis of a tertiary benzylic carbon center via phenol-directed alkene hydrogenation.
    Author: Caille S, Crockett R, Ranganathan K, Wang X, Woo JC, Walker SD.
    Journal: J Org Chem; 2011 Jul 01; 76(13):5198-206. PubMed ID: 21630712.
    Abstract:
    An expeditious synthetic approach to chiral phenol 1, a key building block in the preparation of a series of drug candidates, is reported. The strategy includes a cost-effective and readily scalable route to cyclopentanone 3 from isobutyronitrile (10). The sterically hindered and enolizable ketone 3 was subsequently employed in a challenging Grignard addition mediated by LaCl(3)·2LiCl. A novel preparation of the lanthanide reagent required for this transformation is described. To complete the process, a highly enantioselective hydrogenation step afforded the target (1). The importance of the phenol group to the success of this asymmetric transformation is discussed.
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