Journal of the American Chemical Society
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Scheme 3. Scope of cross-coupling reactions of iodo-
AUTHOR INFORMATION
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benzene with monosaccharides
Corresponding Author
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Author Contributions
†These authors contributed equally
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ACKNOWLEDGMENT
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This work was supported by the University of Colorado
Boulder. Prof. T. Sammakia is thanked for helpful discusꢀ
sions.
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General reaction conditions were adopted from Table 1, entry 9.
All anomeric stannanes were used as a single diastereoisomer (dr
>99:1, 1H NMR). am-xylene, 140 oC.
To conclude, we described here the first example of a
direct stereospecific synthesis of aryl Cꢀglycosides using
anomeric stannanes. In a broader context, our results
demonstrate unprecedented control of the anomeric conꢀ
figuration enabled by a stereospecific crossꢀcoupling
reaction with C1 stannanes. This technology eliminates
many problems inherent to the previous nucleophilic
displacement methods, and, because of its exceptionally
broad substrate scope and high chemoselectivity, it will
create new opportunities to incorporate saccharides into
small molecules and biologics.18
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ASSOCIATED CONTENT
Supporting Information. The Supporting Inforꢀ
mation is available free of charge on the ACS Publications
website at DOI: Experimental procedures and spectral data
(PDF). This material is available free of charge via the Inꢀ
14. Hicks, J. D.; Hyde, A. M.; Cuezva, A. M.; Buchwald, S. L., J. Am.
Chem. Soc. 2009, 131, 16720ꢀ16734.
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