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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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Article information


Submitted
05 Apr 2017
Accepted
21 Apr 2017
First published
21 Apr 2017

Org. Biomol. Chem., 2017,15, 4399-4416
Article type
Paper

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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