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 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 74 Issue: 27
  • Publication Date: 2018
  • Doi Number: 10.1016/j.tet.2018.05.017
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.3564-3577

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.