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  • Title: P(NMe2)3-Mediated Umpolung Alkylation and Nonylidic Olefination of α-Keto Esters.
    Author: Wang SR, Radosevich AT.
    Journal: Org Lett; 2015 Aug 07; 17(15):3810-3. PubMed ID: 26176378.
    Abstract:
    A commercial phosphorus-based reagent (P(NMe2)3) mediates umpolung alkylation of methyl aroylformates with benzylic and allylic bromides, leading to either Barbier-type addition or ylide-free olefination products upon workup. The reaction sequence is initiated by a two-electron redox addition of the tricoordinate phosphorus reagent with an α-keto ester compound (Kukhtin-Ramirez addition). A mechanistic rationale is offered for the chemoselectivity upon which the success of this nonmetal mediated C-C bond forming strategy is based.
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