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  • Title: Catalytic asymmetric γ-alkylation of carbonyl compounds via stereoconvergent Suzuki cross-couplings.
    Author: Zultanski SL, Fu GC.
    Journal: J Am Chem Soc; 2011 Oct 05; 133(39):15362-4. PubMed ID: 21913638.
    Abstract:
    With the aid of a chiral nickel catalyst, enantioselective γ- (and δ-) alkylations of carbonyl compounds can be achieved through the coupling of γ-haloamides with alkylboranes. In addition to primary alkyl nucleophiles, for the first time for an asymmetric cross-coupling of an unactivated alkyl electrophile, an arylmetal, a boronate ester, and a secondary (cyclopropyl) alkylmetal compound are shown to couple with significant enantioselectivity. A mechanistic study indicates that cleavage of the carbon-halogen bond of the electrophile is irreversible under the conditions for asymmetric carbon-carbon bond formation.
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