Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings
Author(s)
Fu, Gregory C.; Zultanski, Susan
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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.
Date issued
2011-09Department
Massachusetts Institute of Technology. Department of ChemistryJournal
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.
Version: Author's final manuscript
ISSN
0002-7863
1520-5126