The rhodium(II) carbenoid cyclization-cycloaddition cascade of alpha-diazo dihydroindolinones for the synthesis of novel azapolycyclic ring systems

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England D. B., Eagan J. M., Merey G., Anac M., Padwa A.

TETRAHEDRON, cilt.64, sa.6, ss.988-1001, 2008 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 64 Sayı: 6
  • Basım Tarihi: 2008
  • Doi Numarası: 10.1016/j.tet.2007.10.038
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.988-1001
  • Marmara Üniversitesi Adresli: Hayır

Özet

Tandem carbonyl ylide formation-1,3-dipolar cycloaddition of alpha-diazo N-acetyl-tetrahydro-beta-carbolin-1-one derivatives occur efficiently in the presence of a dirhodium catalyst to afford bimolecular cycloadducts in high yield. The Rh(II)-catalyzed reaction also takes place intramolecularly to give products derived from trapping of the carbonyl ylide dipole with a tethered alkene. The power of the intramolecular cascade sequence is that it rapidly assembles a pentacyclic ring system containing three new stereocenters and two adjacent quaternary centers stereospecifically in a single step and in high yield. (c) 2007 Elsevier Ltd. All rights reserved.