Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings
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Author(s)
Fu, Gregory C.
Zultanski, Susan
Date Issued
September 2011
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Zultanski, Susan L., and Gregory C. Fu. “Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings.” Journal of the American Chemical Society 133, no. 39 (October 5, 2011): 15362-15364.
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Author's final manuscript
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja2079515
