[en] The synthesis of very long helical aromatic amide foldamers was thought to be limited by steric hindrance associated with stable folded conformations. This difficulty may be overcome by using pure reagents, relatively high concentrations, and long reaction times. Bromine substituents and careful identification and elimination of anhydride byproducts both greatly improve chromatographic purification, giving access to pure products amenable to a segment-doubling synthesis of sequences composed of up to 96 monomers. An efficient one-pot multibromination of helical oligomers is also reported.
Delsuc, N.; Massip, S.; Léger, J.-M.; Kauffmann, B.; Huc, I. J. Am. Chem. Soc. 2011, 133, 3165 10.1021/ja110677a
Byrne, L.; Solà, J.; Boddaert, T.; Marcelli, T.; Adams, R. W.; Morris, G. A.; Clayden, J. Angew. Chem., Int. Ed. 2014, 53, 151 10.1002/anie.201308264
Pinheiro, V. B.; Taylor, A. I.; Cozens, C.; Abramov, M.; Renders, M.; Zhang, S.; Chaput, J. C.; Wengel, J.; Peak-Chew, S. Y.; McLaughlin, S. H.; Herdewijn, P.; Holliger, P. Science 2012, 336, 341 10.1126/science.1217622
Kimoto, M.; Yamashige, R.; Matsunaga, K.-i.; Yokoyama, S.; Hirao, I. Nat. Biotechnol. 2013, 31, 453 10.1038/nbt.2556
