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Issue 20, 2017
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Cationic polycyclization of ynamides: building up molecular complexity

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Abstract

Polycyclization reactions are among the most efficient synthetic tools for the synthesis of complex, polycyclic molecules in a single operation from simple starting materials. We report in this manuscript a full account on the discovery and development of a novel cationic polycyclization from readily available ynamides. Simple activation of these building blocks under acidic conditions enables the generation of highly reactive activated keteniminium ions, which triggers an unprecedented cationic polycyclization yielding highly substituted polycyclic nitrogen heterocycles possessing up to seven fused cycles and three contiguous stereocenters.

Graphical abstract: Cationic polycyclization of ynamides: building up molecular complexity

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Publication details

The article was received on 05 Apr 2017, accepted on 21 Apr 2017 and first published on 21 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00850C
Citation: Org. Biomol. Chem., 2017,15, 4399-4416
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    Cationic polycyclization of ynamides: building up molecular complexity

    C. Theunissen, B. Métayer, M. Lecomte, N. Henry, H. Chan, G. Compain, P. Gérard, C. Bachmann, N. Mokhtari, J. Marrot, A. Martin-Mingot, S. Thibaudeau and G. Evano, Org. Biomol. Chem., 2017, 15, 4399
    DOI: 10.1039/C7OB00850C

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