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Synfacts 2010(8): 0965-0965  
DOI: 10.1055/s-0030-1257791
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

ZnCl2/Al2O3-Catalyzed Ferrier Azaglycosylation

Contributor(s): Yasuhiro Uozumi, Haifeng Zhou
F. Ding, R. William, B. K. Gorityala, J. Ma, S. Wang, X.-W. Liu*
Nanyang Technological University, Singapore
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Publikationsdatum:
22. Juli 2010 (online)

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Significance

ZnCl2/Al2O3 catalyzed Ferrier azaglycosylation of tri-O-acetyl-d-glucal (1) with various N-nucleophiles 2 (sulfonamides, carbamates, amides, and azides) to give the corresponding 2,3-unsaturated N-pseudoglycals 3 in up to 96% yield with high α-anomeric selectivity (13 examples). The catalyst could be recycled up to three times.