Semipinacol rearrangement of cis-fused β-lactam diols into keto-bridged bicyclic lactams.

@article{Grainger2012SemipinacolRO,
  title={Semipinacol rearrangement of cis-fused β-lactam diols into keto-bridged bicyclic lactams.},
  author={Richard S Grainger and Marie Betou and Louise Male and Mateusz B. Pitak and Simon J. Coles},
  journal={Organic letters},
  year={2012},
  volume={14 9},
  pages={2234-7}
}
The 6-azabicyclo[3.2.1]octane ring system, prevalent in a range of biologically active molecules, is prepared through a novel semipinacol rearrangement utilizing a cyclic phosphorane or sulfite intermediate. The rearrangement proceeds with exclusive N-acyl group migration of a β-lactam ring and results in carbonyl functionality at the 7- and bridging 8… CONTINUE READING