Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States
J. Am. Chem. Soc., Article ASAP
DOI: 10.1021/jacs.6b03384
Publication Date (Web): June 08, 2016
Copyright © 2016 American Chemical Society
Abstract
Nickel-catalyzed
enantioselective cross-couplings between symmetric cyclic sulfates and
aromatic Grignard reagents are described. These reactions are effective
with a broad range of substituted cyclic sulfates and deliver products
with asymmetric tertiary carbon centers. Mechanistic experiments point
to a stereoinvertive SN2-like oxidative addition of a nickel complex to the electrophilic substrate.
enantioselective cross-couplings between symmetric cyclic sulfates and
aromatic Grignard reagents are described. These reactions are effective
with a broad range of substituted cyclic sulfates and deliver products
with asymmetric tertiary carbon centers. Mechanistic experiments point
to a stereoinvertive SN2-like oxidative addition of a nickel complex to the electrophilic substrate.
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