Brønsted acid catalyzed regioselective aza-Ferrier reaction: a novel synthetic method for alpha-(N-Boc-2-pyrrolidinyl) aldehydes.

@article{Tayama2008BrnstedAC,
  title={Br\onsted acid catalyzed regioselective aza-Ferrier reaction: a novel synthetic method for alpha-(N-Boc-2-pyrrolidinyl) aldehydes.},
  author={Eiji Tayama and Seijun Otoyama and Wataru Isaka},
  journal={Chemical communications},
  year={2008},
  volume={35},
  pages={4216-8}
}
The 1,4-elimination reaction of (Z)-N-Boc-2-(4-methoxy-2-alkenyloxy)pyrrolidines is shown to proceed with high (1E,3E)-stereoselectivity to afford N-Boc-2-(1,3-dienyloxy)pyrrolidines; the Brønsted acid catalyzed aza-Ferrier reaction of the N-Boc-2-(1,3-dienyloxy)pyrrolidines (3) provides alpha-(N-Boc-2-pyrrolidinyl) aldehydes in excellent yields with high alpha-regioselectivities.