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Regioselective 1,2-additions of alcohols to allenamides mediated by N-Iodosuccinimide: Synthesis of N,O-aminals

Author:
Yuan, Xiao, Re He Man, Xi Jia Ai Ti, Li, Xiao-Xiao, Zhao, Zhi-Gang
Source:
Tetrahedron 2018 v.74 no.39 pp. 5674-5682
ISSN:
0040-4020
Subject:
Lewis bases, alcohols, chemical reactions, chemical structure, regioselectivity, solvents
Abstract:
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.
Agid:
6103549