7054
M. Adinolfi et al. / Tetrahedron Letters 50 (2009) 7051–7054
A.; Schiattarella, M. Org. Lett. 2003, 5, 987–989; For an application to
a
Acknowledgment
biologically relevant target: (c) Adinolfi, M.; Iadonisi, A.; Ravidà, A.;
Schiattarella, M. J. Org. Chem. 2005, 70, 5316–5319.
NMR and MS facilities of CIMCF (‘Centro Interdipartimentale di
Metodologie Chimico-Fisiche’) are acknowledged.
8. For a recent example of a sterically bulky participating groups for 1,2-trans
glycosidations: Szpilman, A. M.; Carreira, E. M. Org. Lett. 2009, 11, 1305–1307.
9. For a recent report on the generation of saccharidic cyclic carbonates arising
from participation effects: Crich, D.; Hu, T.; Cai, F. J. Org. Chem. 2008, 73, 8942–
8953.
Supplementary data
10. Bouzbouz, S.; Kirschleger, B. Synthesis 1994, 714–718.
11. For some examples: (a) Mayato, C.; Dorta, R. L.; Vazquez, J. T. Tetrahedron
Lett. 2008, 49, 1396–1398; (b) Fisher, J. W.; Trinkle, K. L. Tetrahedron Lett.
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Experimental procedures, spectroscopic data and copies of NMR
spectra of all the products are available. Supplementary data asso-
ciated with this article can be found, in the online version, at
References and notes
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18. Experimental procedure: The saccharidic compound (0.3 mmol) and LiI (120 mg,
0.9 mmol) were dissolved in pyridine (1.4 mL) and to the resulting solution
was added acetic acid (90
lL, 1.5 mmol). The resulting mixture was refluxed
for the times indicated on Table 1, and then the vessel was cooled to rt. The
mixture was diluted with DCM and the organic phase was washed with water.
The aqueous phase was re-extracted with DCM and ethyl acetate. The collected
organic phases were dried and concentrated in vacuo to give a residue which
was purified by silica gel flash chromatography (eluent: petroleum ether/ethyl
acetate mixtures).
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