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, cilt.57, sa.32, ss.7035-7045, 2001 (SCI İndekslerine Giren Dergi) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 57 Konu: 32
  • Basım Tarihi: 2001
  • Dergi Adı: TETRAHEDRON
  • Sayfa Sayıları: ss.7035-7045

Özet

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.