Endo entry to the nortricyclyl-norbornenyl cation system: stereochemistry in the fragmentation of endo-5-norbornenyl-2-oxychlorocarbene.

@article{Moss2005EndoET,
  title={Endo entry to the nortricyclyl-norbornenyl cation system: stereochemistry in the fragmentation of endo-5-norbornenyl-2-oxychlorocarbene.},
  author={Robert A Moss and Xiaolin Fu and Ronald R. Sauers and Peter Wipf},
  journal={The Journal of organic chemistry},
  year={2005},
  volume={70 21},
  pages={8454-60}
}
Fragmentation of (S)-endo-5-norbornenyl-2-oxychlorocarbene [(S)-8] in cyclohexane-d12 gives approximately 20% (S)-endo-2-chloro-5-norbornene [(S)-7] with approximately 50% ee, 65-70% (R)-exo-2-chloro-5-norbornene [(R)-4] with >95% ee, and approximately 12% (R)-3-nortricyclyl chloride [(R)-5] with approximately 22% ee. (Analogous stereochemical results were… CONTINUE READING