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The Lewis acid probably coordinates to the external oxygen atom of the dioxolane moiety of syn/anti-3 leading to a ring opening, and then an attack of the resulting carbenium ion onto the enol ether double bond. Finally fragmentation of the TMSE group generates the central carbonyl group of bicycles 6-8 (see reference [9]).
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The Lewis acid probably coordinates to the external oxygen atom of the dioxolane moiety of syn/anti-3 leading to a ring opening, and then an attack of the resulting carbenium ion onto the enol ether double bond. Finally fragmentation of the TMSE group generates the central carbonyl group of bicycles 6-8 (see reference [9]).
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31
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First experiments reveal that phenylseleno-substituted 1,2-oxazines may also be used: F. Pfrengle, H.-U. Reissig, unpublished results.
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First experiments reveal that phenylseleno-substituted 1,2-oxazines may also be used: F. Pfrengle, H.-U. Reissig, unpublished results.
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70349971331
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The TBSOTf-induced rearrangement was unsuccessful in case of anti-3.
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The TBSOTf-induced rearrangement was unsuccessful in case of anti-3.
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These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
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CCDC 708522 (15) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/data-request/cif.
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CCDC 708522 (15) contains the supplementary crystallographic data for this paper
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The synthesis of non-glycosidic compounds is also possible. This possibility could serve for the construction of linear or branched oligosaccharide mimetics (see F. Sicherl, V. Wittmann, Angew. Chem. 2005, 117, 2133-2136; Angew. Chem. Int. Ed. 2005, 44, 2133-2136) or achieve the geometrically defined presentation of ligands (see U. Hünger, J. Ohnsmann, H. Kunz, Angew. Chem. 2004, 116, 1125-1128; Angew. Chem. Int. Ed. 2004, 43, 1104-1107).
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The synthesis of non-glycosidic compounds is also possible. This possibility could serve for the construction of linear or branched oligosaccharide mimetics (see F. Sicherl, V. Wittmann, Angew. Chem. 2005, 117, 2133-2136; Angew. Chem. Int. Ed. 2005, 44, 2133-2136) or achieve the geometrically defined presentation of ligands (see U. Hünger, J. Ohnsmann, H. Kunz, Angew. Chem. 2004, 116, 1125-1128; Angew. Chem. Int. Ed. 2004, 43, 1104-1107).
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