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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

Authors :
Colin A. Kilner
H. Ali Dondas
Emma L. Millington
R. Grigg
Colin W. G. Fishwick
Source :
Tetrahedron. 74:3564-3577
Publication Year :
2018
Publisher :
Elsevier BV, 2018.

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.

Details

ISSN :
00404020
Volume :
74
Database :
OpenAIRE
Journal :
Tetrahedron
Accession number :
edsair.doi...........205a36f3742656d1d52cc9e2460b0c66
Full Text :
https://doi.org/10.1016/j.tet.2018.05.017