Synthesis of Pyrrolidines by a Three-Component Reaction

Significance

Reported is the synthesis of highly substituted pyrrolidines by a three-component reaction of nitroalkenes, aminomalonates, and aldehydes. A reasonable mechanism is proposed, with formation of the iminoester and its equilibration to a Huisgen-like 1,3-dipole preceding the [2+3] cycloaddition reaction with the nitroalkene. Although the formation of pyrrolidines through [2+3] cycloaddition of iminoesters and nitroalkenes is known, they commonly require high temperatures or metal catalysts.