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


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

TETRAHEDRON, vol.64, no.6, pp.988-1001, 2008 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 64 Issue: 6
  • Publication Date: 2008
  • Doi Number: 10.1016/j.tet.2007.10.038
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.988-1001

Abstract

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.