Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 26, Pages 7888-7892Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201802159
Keywords
cis amides; fluxionality; frustrated helicity; macrocycles; strained structures
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Funding
- JSPS KAKENHI Grant [16K08318, 17J00036]
- Sumitomo Foundation
- Naito Foundation
- NSF grant [MRI CHE-1229564]
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Macrocyclization of a stable two-turn helical aromatic pentamide, that is, an object with diverging ends that are not prone to cyclization, was made possible by the transient introduction of disruptors of helicity in the form of acid-labile dimethoxybenzyl tertiary amide substituents. After removal of the helicity disruptors, NMR, X-ray crystallography, and computational studies show that the macrocycle possesses a strained structure that tries to gain as high a helical content as possible despite being cyclic. Two points of disruption of helicity remain, in particular a cis amide bond. This point of disruption of helicity can propagate along the cycle in a fluxional manner according to defined trajectories to produce ten degenerate conformations.
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