%0 Generic %A Pohlhaus, Patrick D. %A Bowman, Roy K. %A Johnson, Jeffrey S. %D 2004 %T Lewis Acid-Promoted Carbon−Carbon Bond Cleavage of Aziridines:  Divergent Cycloaddition Pathways of the Derived Ylides %U https://acs.figshare.com/articles/dataset/Lewis_Acid_Promoted_Carbon_Carbon_Bond_Cleavage_of_Aziridines_Divergent_Cycloaddition_Pathways_of_the_Derived_Ylides/3348223 %R 10.1021/ja0397963.s001 %2 https://ndownloader.figshare.com/files/5187535 %K Derived Ylides Lewis acids %K pyrrolidine products %K Cycloaddition Pathways %K ambient temperature %K ylide %K cycloaddition reactions %K Cyclic alkenes %K acyclic alkenes %X 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. %I ACS Publications