Extending Pummerer reaction chemistry. development of a strategy for the regio- and stereoselective oxidative cyclization of 3-(omega-nucleophile)-tethered indoles.

@article{Feldman2005ExtendingPR,
  title={Extending Pummerer reaction chemistry. development of a strategy for the regio- and stereoselective oxidative cyclization of 3-(omega-nucleophile)-tethered indoles.},
  author={Ken S. Feldman and Daniela Boneva Vidulova and Andrew G Karatjas},
  journal={The Journal of organic chemistry},
  year={2005},
  volume={70 16},
  pages={6429-40}
}
The brominative cyclization of diastereomeric beta-silyloxy tryptophan derivatives proceeded with divergent regiochemistry (C(2) or C(3) addition), depending on the relative stereochemistry of the silyloxy substituent. This lack of C(2) vs C(3) regiochemical predictability led to the development of a new approach, which featured Pummerer-type chemistry on… CONTINUE READING