N-heterocycles from oxime and oxime O-benzyl ethers via electrophile induced-ring formation. Route to cyclic and bicyclic amine and hydroxylamine

Dondas H. A., Yaktubay N.

HETEROCYCLIC COMMUNICATIONS, vol.9, no.4, pp.337-344, 2003 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 9 Issue: 4
  • Publication Date: 2003
  • Doi Number: 10.1515/hc.2003.9.4.337
  • Journal Name: HETEROCYCLIC COMMUNICATIONS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.337-344
  • Çukurova University Affiliated: No

Abstract

Phenylselenyl and iodine induced chiral and achiral ring forming cyclisations creating bridged bicyclo-[3.2.1]- and cyclic ring N-hydroxylamines and bicyclo-[3.2.1]- ring amines occur stereo-, regio- and facially specifically that involve multiplication of chiral centres from one to two and three in one pot reactions in moderate to good yield. An example of bromine induced cyclisation and 1,3-dipolar cycloaddition creating isoxazolidine-ring were also reported.