Type 2 intramolecular nitroso Diels-Alder reaction. Synthesis and structure of bridgehead oxazinolactams

Org Lett. 2000 May 18;2(10):1473-5. doi: 10.1021/ol005811m.


[reaction--see text] The type 2 intramolecular Diels-Alder cycloaddition utilizing N-acylnitroso dienophiles provides an efficient entry into bridged oxazinolactams. In contrast to the bimolecular counterpart, the reaction is completely regioselective. Structural characterization of the cycloadducts allows for evaluation of the olefin distortion and the degree of pyramidalization of the bridgehead oxazinolactam.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Indicators and Reagents
  • Lactams / chemical synthesis*
  • Lactams / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Nitroso Compounds*
  • Oxazines / chemical synthesis*
  • Oxazines / chemistry


  • Indicators and Reagents
  • Lactams
  • Nitroso Compounds
  • Oxazines