Cycloaddition reactions of aldimines of 1,5-ketoaldehydes. Applications in the synthesis of polycyclic nitrogen heterocycles

Article abstract of DOI:10.1016/S0040-4020(98)01189-2

Aliphatic aldimines of a range of cyclic and acyclic 1,5-ketoaldehydes undergo metal catalysed regio- and stereo-specific imine → azomethine ylide → cycloaddition cascades. Acid catalysed cyclisations of the NH group of the pyrrolidine products onto the ketone functionality results in novel tri- and tetra-cyclic nitrogen heterocycles.