X=Y-ZH Systems as potential 1,3-dipoles. Part 52: Fused-ring forming electrophile induced oxime -> nitrone -> cycloaddition cascades

DÖNDAŞ H. A., Grigg R., Thibault S.

TETRAHEDRON, vol.57, no.32, pp.7035-7045, 2001 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 57 Issue: 32
  • Publication Date: 2001
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.7035-7045
  • Çukurova University Affiliated: No

Abstract

Electrophile induced cyclisation of oximes onto endocyclic alkenes and exo-methylene cycloalkanes occurs stereo- and regiospecifically generating cis-fused bicyclic nitrones in good yield. Subsequent facially selective cycloaddition with N-methylmaleimide occurs in good yield. The sequence may be carried out as a one-pot procedure and results in the formation of 4 bonds, 2 rings and 6 stereocentres. (C) 2001 Elsevier Science Ltd. All rights reserved.