A cascade approach to cyclic aminonitrones: reaction discovery, mechanism, and scope

Org Lett. 2009 Aug 6;11(15):3194-7. doi: 10.1021/ol9010147.

Abstract

Treatment of omega-epoxynitriles with hydroxylamine affords cyclic aminonitrones in a single step and with high stereoselectivity. The scope of this novel transformation was explored in a series of examples. The aminonitrone products were shown to be useful substrates for further selective elaboration.

MeSH terms

  • Crystallography, X-Ray
  • Cyclization
  • Drug Design
  • HIV Integrase Inhibitors / chemical synthesis
  • HIV Integrase Inhibitors / chemistry*
  • Molecular Structure
  • Pyrimidinones / chemical synthesis
  • Pyrimidinones / chemistry*
  • Pyrrolidinones / chemistry
  • Raltegravir Potassium

Substances

  • HIV Integrase Inhibitors
  • Pyrimidinones
  • Pyrrolidinones
  • Raltegravir Potassium