Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening–Formal [3 + 2] Cycloaddition

Giada Arena, C Chun Chen, Daniele Leonori, Varinder K Aggarwal

    Research output: Contribution to journalArticlepeer-review

    Abstract

    3-Methyl vinyl aziridine undergoes a mild MgI2-promoted SN2′ ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.
    Original languageEnglish
    Pages (from-to)4250-4253
    Number of pages3
    JournalOrganic Letters
    Volume15
    Issue number16
    DOIs
    Publication statusPublished - 2 Aug 2013

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