X=Y-ZH systems as potential 1,3-dipoles. Part 53: Sequential nucleophilic ring opening-1,3-dipolar cycloaddition reactions of Z-oxime anions with aziridines and dipolarophiles

DÖNDAŞ H. A., Cummins J., Grigg R., Thornton-Pett M.

TETRAHEDRON, vol.57, no.37, pp.7951-7964, 2001 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 57 Issue: 37
  • Publication Date: 2001
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.7951-7964
  • Çukurova University Affiliated: No

Abstract

Nucleophilic ring opening of aziridines involving attack of the nitrogen atom of Z-oxime anions generates nitrones which are then trapped in 1,3-dipolar cycloaddition reactions with N-methylmaleimide to afford 1: 1 mixture of endo- and exo-cycloadducts. (C) 2001 Elsevier Science Ltd. All rights reserved.