Multicomponent domino [4+2]/[3+2] cycloadditions of nitroheteroaromatics: an efficient synthesis of fused nitrogenated polycycles.
Activation by high pressure allows 3-nitroindole and 3-nitropyrrole derivatives to behave as electron-poor heterodienes in multicomponent domino [4+2]/[3+2] cycloaddition processes. The primary [4+2] inverse demand cycloaddition appears to be completely endo selective, while the subsequent [3+2] process shows a total facial selectivity, setting the stereochemistry at ring junction, and an endo/exo selectivity depending on the nature of the heterocycle. In two operations, a polycyclic diamine featuring a quaternary center at ring junction is efficiently generated.
Chataigner
Isabelle
I
Université de Rouen, UMR CNRS 6014, F-76821 Mont Saint Aignan, France. isabelle.chataigner@univ-rouen.fr
Piettre
Serge R
SR