Diverging chemoselective reactions of separable amide rotational isomers.

@article{Li2010DivergingCR,
  title={Diverging chemoselective reactions of separable amide rotational isomers.},
  author={Xiben Li and Dennis P Curran},
  journal={Organic letters},
  year={2010},
  volume={12 3},
  pages={612-4}
}
Diverging chemoselective reactions of a pair of amide rotamers have been observed by separating the rotamers and then reacting them individually. Reduction of (Z)-N-allyl-2-(phenylselanyl)-N-(2,4,6-tri-tert-butylphenyl)acetamide with tributyltin hydride at room temperature provides only the product of 5-exo cyclization, 4-methyl-1-(2,4,6-tri-tert-butylphenyl)pyrrolidin-2-one. In contrast, reduction of the corresponding (E) amide rotational isomer under identical conditions provides only the… CONTINUE READING