Organocatalytic Asymmetric Synthesis of C-N Atropisomers with Pyrrole, Oxindole and Succinimide Scaffold.

An asymmetric synthesis of C-N atropisomers with pyrrole, oxindole and succinimide moities was developed via organocatalytic desymmetric Michael addition of 3-pyrrolyloxindole with prochiral N-aryl maleimides. The C-N atropisomers were obtained in acceptable yields with high diastero- and enantioselectivities (>20 : 1 dr, up to >99 % ee). C-N Rotational energy barrier has also been determined.