Silylated pyrrolidones via diastereoselective Pd-catalysed intramolecular allylic alkylations

Giovanni Poli, Giuliano Giambastiani, Max Malacria, Serge Thorimbert
  • Tetrahedron Letters, September 2001, Elsevier
  • DOI: 10.1016/s0040-4039(01)01249-7

What is it about?

A new palladium-catalysed allylic alkylation affording silylated 3-vinyl-pyrrolidones has been developed. The method relies upon the interaction between a stabilised acetamide enolate anion and a silicon-containing nitrogen-tethered η3-allyl-palladium moiety. Two variants have been studied, involving location of the silicon atom on either olefinic carbon atom of the cyclisation precursor. In both cases 5-exo-trig ring closure was the only cyclisation process observed. These results contrast with related β-ketoester cyclisations, were competitive 7-endo-trig is observed.

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The following have contributed to this page: Professor Serge THORIMBERT and Dr Giuliano Giambastiani