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Regioselective 1,2-additions of alcohols to allenamides mediated by N-Iodosuccinimide: Synthesis of N,O-aminals
- Yuan, Xiao, Re He Man, Xi Jia Ai Ti, Li, Xiao-Xiao, Zhao, Zhi-Gang
- Tetrahedron 2018 v.74 no.39 pp. 5674-5682
- Lewis bases, alcohols, chemical reactions, chemical structure, regioselectivity, solvents
- N,O-Aminals are synthesized through the N-iodosuccinimide-mediated regioselective 1,2-additions of alcohols to allenamides. These novel reactions proceed rapidly and exhibit broad substrate scope for a variety of allenamides. The reaction demonstrates that N-Iodosuccinimide is effective in activating the terminal CC bond of allenamides generating conjugated sulfamide ion species. It is noteworthy that the alcohol served as both solvent and nucleophile in this transformation.