(2,5)-Ene cyclization catalyzed by mesoporous solid acids: isotope labeling study and ab initio calculation for continuum from concerted to stepwise ene mechanism.

@article{Mikami200325EneCC,
  title={(2,5)-Ene cyclization catalyzed by mesoporous solid acids: isotope labeling study and ab initio calculation for continuum from concerted to stepwise ene mechanism.},
  author={Koichi Mikami and Hirofumi Ohmura and Masahiro Yamanaka},
  journal={The Journal of organic chemistry},
  year={2003},
  volume={68 3},
  pages={1081-8}
}
(2,5)-Ene reactions catalyzed by mesoporous solid acids are reported from the mechanistic point of view. The continuum (2,5)-ene mechanism from the concerted to the cationic cyclization followed by 1,2-hydride shift is evaluated. The solid-acid-catalyzed cyclization of the oxonium ion intermediate 4 derived from cyclic allylic lactol ether 3 bearing allylic hydroxy group affords the (2,5)-ene product as the enol form, eventually tautomerizing to the corresponding aldehyde 6. The continuum from… CONTINUE READING

From This Paper

Topics from this paper.
0 Citations
0 References
Similar Papers

Similar Papers

Loading similar papers…