An unreported 5-endo-trig atom transfer radical cyclization of cyclic N--dichloroacyl-ketene-N,S-acetals, which evolves as a tandem radical-polar process, is described. The reaction, which is carried out in the presence of a Cu(I) complex catalyst (10 mol%) and an inorganic base (i.e. carbonate), can be exploited as the key step for a novel, short and versatile synthesis of the 3,4-disubstituted maleic anhydride nucleus.
Synthesis of the disubstituted maleic anhydride frame using a novel tandem radical-polar reaction / Pattarozzi, Mariella; Ghelfi, Franco; Roncaglia, Fabrizio; Pagnoni, Ugo Maria; A. F., Parsons. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - 00:13(2009), pp. 2172-2176. [10.1055/s-0029-1217569]
Synthesis of the disubstituted maleic anhydride frame using a novel tandem radical-polar reaction
PATTAROZZI, Mariella;GHELFI, Franco;RONCAGLIA, Fabrizio;PAGNONI, Ugo Maria;
2009
Abstract
An unreported 5-endo-trig atom transfer radical cyclization of cyclic N--dichloroacyl-ketene-N,S-acetals, which evolves as a tandem radical-polar process, is described. The reaction, which is carried out in the presence of a Cu(I) complex catalyst (10 mol%) and an inorganic base (i.e. carbonate), can be exploited as the key step for a novel, short and versatile synthesis of the 3,4-disubstituted maleic anhydride nucleus.
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