Stereoselective Synthesis of 3,4-trans-Disubstituted γ-Lactams by Cerium(IV) Ammonium Nitrate Mediated Radical Cyclization of Cinnamamides
12 March 2007 (eFirst)
A facile synthesis of 3,4-trans-disubstituted γ-lactams was developed, consisting of the radical cyclization of cinnamamides mediated by cerium(IV) ammonium nitrate. The single-electron-transfer (SET) reaction of the methoxystyrenyl moiety mediated by cerium(IV) ammonium nitrate gives rise to a cation radical, whose cyclization followed by reaction with oxygen and methanol generates 3,4-trans-disubstituted γ-lactams.
cerium(IV) ammonium nitrate - intramolecular cyclization - cinnamamides - single electron transfer - γ-lactams