The α-effect in iminium ion catalysis

Article abstract of DOI:10.1016/j.tet.2005.08.110

The α-effect can be used as an effective means to promote iminium ion catalysed transformations, providing acyclic scaffolds to aid in catalyst design. A thorough investigation of the structure-activity relationship of the catalyst architecture reveals optimal substituents of a disubstituted carbamate and a secondary alkyl group around a hydrazine scaffold. Molecular modelling investigations provide a mechanistic rationale to the results observed.