Robust trans-amide helical structure of oligomers of bicyclic mimics of β-proline: impact of positional switching of bridgehead substituent on amide cis-trans equilibrium.

@article{Wang2014RobustTH,
  title={Robust trans-amide helical structure of oligomers of bicyclic mimics of β-proline: impact of positional switching of bridgehead substituent on amide cis-trans equilibrium.},
  author={Siyuan Wang and Yuko Otani and Xin Liu and Masatoshi Kawahata and Kentaro Yamaguchi and Tomohiko Ohwada},
  journal={The Journal of organic chemistry},
  year={2014},
  volume={79 11},
  pages={5287-300}
}
Because homooligomers of 7-azabicyclo[2.2.1]heptane-2-endo-carboxylic acid, a bridged β-proline analogue with a substituent installed at the remote C4-bridgehead position, completely biased the amide cis-trans equilibrium to the cis-amide structure, we expected that introduction of a substituent at the C1-bridgehead position adjacent to the carboxylic acid moiety, rather than the remote C4-bridgehead position, would tip the cis-trans amide equilibrium toward trans-amide structure without the… CONTINUE READING
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