Abstract

AbstractThe nitro‐Michael addition of organolithium species to 2‐nitroglycal derivatives was investigated. This methodology affords straightforward and stereoselective access to C‐nitroglycosides, which are excellent precursors to C–N‐acetylglycosamines. The corresponding products bearing an aromatic, heteroaromatic, alkynyl, alkenyl, or alkyl moiety were isolated in good yields with excellent selectivities. The β isomer was isolated as a single stereoisomer in most cases, and the structure was clearly elucidated by NMR spectroscopy experiments.

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