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 3-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 -ketoester cyclisations, were competitive 7-endo-trig is observed.
Silylated pyrrolidones via diastereoselective Pd-catalysed intramolecular allylic alkylations / Poli G; Giambastiani G; Malacria M; Thorimbert S. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 42:(2001), pp. 6287-6289. [10.1016/S0040-4039(01)01249-7]
Silylated pyrrolidones via diastereoselective Pd-catalysed intramolecular allylic alkylations
Giambastiani G;
2001
Abstract
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 3-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 -ketoester cyclisations, were competitive 7-endo-trig is observed.File | Dimensione | Formato | |
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