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      https://www.ias.ac.in/article/fulltext/jcsc/128/01/0111-0117

    • Keywords

       

      𝛽-Lactam; [2+2] Cycloaddition; Benzyl-𝑁-pyrrolylketene; NMR; NOE; Diasteroselectivity.

    • Abstract

       

      3-Phenyl-2-(1-𝐻-pyrrol-1-yl) propanoic acid has been used as a ketene source in synthesizing of monocyclic-2-azetidinones. Hindrance in ketene and imines successfully controlled the diastereoselectivity of the reaction. For example, in some cases only one isomer was achieved. By using Mukaiyama reagent, the leaving group in acid was activated and the by-products were separated by simple aqueous work-up. DFT calculation indicated that the benzyl-𝑁-pyrrolylketene has nonconjugated structure and the pyrrolyl ring is perpendicular to the ketene plane in both the twisted and planar structures.

    • Author Affiliations

       

      Masoumeh Behzadi1 Kazem Saidi1 Mohammad Reza Islami1 Hojatollah Khabazzadeh1

      1. Department of Chemistry, Shahid Bahonar University of Kerman, Kerman 76169-14111, Iran
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