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A new metal-based method to synthesize C(1)-substituted glycals has been developed. Starting with the obtained substituted C-glycals, the possibility of a stereocontrolled addition (via azidoselenation) to form β-C-substituted-2-aminoglycosides has been investigated. Instead of forming the expected C-glycosyl derivatives of 2-amino sugars, an inseparable mixture of diastereomers, which were derived from the corresponding C(1)-allylated glycals, has been obtained.