Abstract
An unreported 5-endo-trig atom-transfer radical cyclization of cyclic N-alpha-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.
Original language | English |
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Pages (from-to) | 2172-2176 |
Number of pages | 5 |
Journal | Synlett |
Issue number | 13 |
DOIs | |
Publication status | Published - 13 Aug 2009 |
Keywords
- cyclizations
- imides
- radical reactions
- sulfur
- tandem reactions
- N-HETEROCYCLE SYNTHESIS
- ALPHA-HALO AMIDES
- GAMMA-LACTAMS
- SUBSTITUTED PYRROLIDINONES
- FUNCTIONAL REARRANGEMENT
- CHAETOMELLIC ANHYDRIDE
- CYCLIZATION REACTIONS
- MILD CONDITIONS
- CUCL-TMEDA
- 5-ENDO