Synlett

Synthesis of the Disubstituted Maleic Anhydride Frame Using a Novel Tandem Radical-Polar Reaction

M Pattarozzi, F Ghelfi, F Roncaglia, UM Pagnoni…

Index: Pattarozzi, Mariella; Ghelfi, Franco; Roncaglia, Fabrizio; Pagnoni, Ugo M.; Parsonsb, Andrew F. Synlett, 2009 , # 13 p. 2172 - 2176

Full Text: HTML

Citation Number: 5

Abstract

Abstract An unreported 5-endo-trig atom-transfer radical cyclization of cyclic N-α- 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 (ie, carbonate), can be exploited as the key step for a novel, short, and versatile synthesis of the 3, 4-disubstituted maleic anhydride nucleus.

Related Articles:

Chemoselective carbon-carbon coupling of organocuprates with (bromomethyl) methylmaleic anhydride: Synthesis of chaetomellic acid A

[Deshpande, Anil M.; Natu, Arvind A.; Argade, Narshinha P. Journal of Organic Chemistry, 1998 , vol. 63, # 25 p. 9557 - 9558]

Chemoselective carbon-carbon coupling of organocuprates with (bromomethyl) methylmaleic anhydride: Synthesis of chaetomellic acid A

[Deshpande, Anil M.; Natu, Arvind A.; Argade, Narshinha P. Journal of Organic Chemistry, 1998 , vol. 63, # 25 p. 9557 - 9558]

Studies in the biochemistry of micro-organisms. 97. Flavipin, a crystalline metabolite of Aspergillus flavipes (Bainier & Sartory) Thom & Church and Aspergillus terreus …

[Muir; Neuberger Biochemical Journal, 1949 , vol. 45, p. 163,165]

1, 2-Carbonyl migration along the allylic framework: synthesis of alkenylnaphthoquinones

[Mahidol, Chulabhorn; Pinyopronpanit, Yongyut; Radviroongit, Shuleewan; Thebtaranonth, Chachanat; Thebtaranonth, Yodhathai Journal of the Chemical Society, Chemical Communications, 1988 , # 20 p. 1382 - 1383]

More Articles...