Organic Letters
Letter
mechanism in dioxane, while it proceeds in a nonstereose-
lective manner in DMF via an SN1 mechanism. The SN2-type
stereoselective Mitsunobu glycosylation was widely applicable
to glycoside formation between various commercial unpro-
tected pyranoses as glycosyl donors and a variety of acidic
glycosyl acceptors. This glycosylation method using unpro-
tected carbohydrates could be applicable to glycodiversification
of medicinally important molecules.20,21
ACKNOWLEDGMENTS
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This research was financially supported by Grants-in-Aid for
Scientific Research S (JP26221301), Young Scientists B
(JP15K18827), and Scientific Research on Innovative Areas
‘Advanced Molecular Transformation by Organocatalysts’
(JP23105008) and ‘Middle Molecular Strategy’
(JP16H01148). Y.U. acknowledges financial support from
the Naito Foundation. H.T. is thankful for financial support
received through JSPS Research Fellowships for Young
Scientists (JP13J03416). The authors also thank Ms. Ayaka
Maeno (Institute for Chemical Research, Kyoto University) for
assistance with quantitative 13C NMR spectroscopy.
ASSOCIATED CONTENT
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* Supporting Information
The Supporting Information is available free of charge at
REFERENCES
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Experimental details, spectral data, and characterization
data for all new compounds (PDF)
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Accession Codes
CCDC 1445049 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
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AUTHOR INFORMATION
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Corresponding Author
Takeo Kawabata − Institute for Chemical Research, Kyoto
Authors
Hironori Takeuchi − Institute for Chemical Research, Kyoto
University, Kyoto 611-0011, Japan
Yusuke Fujimori − Institute for Chemical Research, Kyoto
University, Kyoto 611-0011, Japan
Yoshihiro Ueda − Institute for Chemical Research, Kyoto
Hiromitsu Shibayama − Institute for Chemical Research, Kyoto
University, Kyoto 611-0011, Japan
Masaru Nagaishi − Institute for Chemical Research, Kyoto
University, Kyoto 611-0011, Japan
Tomoyuki Yoshimura − Institute for Chemical Research, Kyoto
University, Kyoto 611-0011, Japan
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Takahiro Sasamori − Institute for Chemical Research, Kyoto
Norihiro Tokitoh − Institute for Chemical Research, Kyoto
Takumi Furuta − Institute for Chemical Research, Kyoto
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Complete contact information is available at:
Author Contributions
†H.T. and Y.F. contributed equally to this work.
Notes
(20) Thibodeaux, C. J.; Melanco
Int. Ed. 2008, 47, 9814.
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n, C. E., III; Liu, H. Angew. Chem.,
The authors declare no competing financial interest.
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