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Lewis Acid-Promoted Carbon−Carbon Bond Cleavage of Aziridines:  Divergent Cycloaddition Pathways of the Derived Ylides

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journal contribution
posted on 03.03.2004, 00:00 by Patrick D. Pohlhaus, Roy K. Bowman, Jeffrey S. Johnson
Lewis acids are shown to cleave the carbon−carbon bond of activated aziridines at ambient temperature. The derived metal-coordinated azomethine ylides undergo cycloaddition reactions with electron-rich alkenes. Cyclic alkenes afford products that are formally [4+2] adducts most likely derived from a Mannich-type addition to the ylide, followed by intramolecular Friedel−Crafts alkylation. Alternatively, acyclic alkenes undergo [3+2] cycloaddition to give new pyrrolidine products.