Guanidinium ylide mediated aziridination: identification of a spiro imidazolidine-oxazolidine intermediate

J Org Chem. 2006 Aug 18;71(17):6600-3. doi: 10.1021/jo060531r.

Abstract

We successfully isolated a spiro imidazolidine-oxazolidine intermediate in the reaction of guanidinium ylide mediated aziridination using alpha-bromocinnamaldehyde. X-ray crystallographic analysis unambiguously revealed that the stereogenic centers of the spiro intermediate were in a trans configuration. The role of the spiro compound as an intermediate in the aziridination reaction was confirmed by observation of its smooth chemical conversion into aziridine products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Aziridines / chemistry*
  • Bromides / chemistry
  • Guanidine / chemical synthesis*
  • Guanidine / chemistry
  • Hydrogen / chemistry
  • Imidazolidines / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Oxazoles / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Aziridines
  • Bromides
  • Imidazolidines
  • Oxazoles
  • oxazolidine
  • alpha-bromocinnamaldehyde
  • aziridine
  • Hydrogen
  • Guanidine