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  • Title: Asymmetric carbon-carbon bond formation gamma to a carbonyl group: phosphine-catalyzed addition of nitromethane to allenes.
    Author: Smith SW, Fu GC.
    Journal: J Am Chem Soc; 2009 Oct 14; 131(40):14231-3. PubMed ID: 19772285.
    Abstract:
    A chiral phosphine catalyzes the addition of a carbon nucleophile to the gamma position of an electron-poor allene (amide-, ester-, or phosphonate-substituted), in preference to isomerization to a 1,3-diene, in good ee and yield. This strategy provides an attractive method for the catalytic asymmetric gamma functionalization of carbonyl (and related) compounds.
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