Catalytic bimetalic [Pd(0)/Ag(I) Heck-1,3-dipolar cycloaddition cascade reactions accessing spiro-oxindoles. Concomitant in situ generation of azomethine ylides and dipolarophile

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Millington E. L., DÖNDAŞ H. A., Fishwick C. W. G., Kilner C., Grigg R.

TETRAHEDRON, vol.74, no.27, pp.3564-3577, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 74 Issue: 27
  • Publication Date: 2018
  • Doi Number: 10.1016/j.tet.2018.05.017
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.3564-3577
  • Çukurova University Affiliated: No

Abstract

Spiro-oxindoles, epi-Spirotryprostatin A and its analogues were prepared from a tactical combination of cascade catalytic bimetallic Pd (0)/Ag(I), intramolecular Heck and subsequent imine -> azomethine ylide -> 1,3-Dipolar cycloaddition reactions. The cascade features in situ generation of azomethine ylides and dipolarophiles and produces two new rings together with three stereocentres in good to excellent yields. (C) 2018 Elsevier Ltd. All rights reserved.