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

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• 作者：Patrick D. Pohlhaus ; Roy K. Bowman ; and Jeffrey S. Johnson
• 刊名：Journal of the American Chemical Society
• 出版年：2004
• 出版时间：March 3, 2004
• 年：2004
• 卷：126
• 期：8
• 页码：2294 - 2295
• 全文大小：66K
• 年卷期：v.126,no.8(March 3, 2004)
• ISSN：1520-5126

文摘

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.