SELENIUM-CATALYZED AND PALLADIUM-CATALYZED OXIDATIVE CLEAVAGE OF ENE-LACTAMS WITH HYDROGEN-PEROXIDE - CONVENIENT METHODS FOR SYNTHESIS OF MACROCYCLIC KETOIMIDES AND N-FUSED AZABICYCLIC COMPOUNDS
T. Naota et al., SELENIUM-CATALYZED AND PALLADIUM-CATALYZED OXIDATIVE CLEAVAGE OF ENE-LACTAMS WITH HYDROGEN-PEROXIDE - CONVENIENT METHODS FOR SYNTHESIS OF MACROCYCLIC KETOIMIDES AND N-FUSED AZABICYCLIC COMPOUNDS, Tetrahedron letters, 34(30), 1993, pp. 4843-4846
Oxidative cleavage of ene-lactams can be performed efficiently by eith
er SeO2 or Pd(OAc)2-catalyzed oxidation with H2O2 to give the correspo
nding ketoimides. The reaction provides convenient methods for the pre
paration of macrocyclic ketoimides and the construction of N-fused aza
bicyclic ring systems such as indolizidine and cephalotaxine skeletons
.