Radical reaction initiated and stereocontrolled by zinc chloride

Yoshinori Yamamoto, Setsuko Onuki, Masatoshi Yumoto, Naoki Asao

    Research output: Contribution to journalArticle

    9 Citations (Scopus)

    Abstract

    The reaction of allyltributyltin with methyl 2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-2-bromoacetate (5 a) was accelerated at -50°C in the presence of AIBN and stopped in the presence of galvinoxyl, indicating that the reaction proceeds through a radical mechanism. The reaction was accelerated dramatically at -78°C in the presence of ZnCl2·OEt2, and the ZnCl2-mediated reaction was stopped in the presence of galvinoxyl. In the presence of 2 equiv ZnCl2·OEt2, the reaction afforded methyl (2R)-2-[N-((4SH-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-4-pentenoate {6a(R)} with high diastereoselectivity (93:7). Taken together, ZnCl2·OEt2 works as a radical initiator as well as chelating agent.

    Original languageEnglish
    Pages (from-to)765-780
    Number of pages16
    JournalHeterocycles
    Volume47
    Issue number2
    DOIs
    Publication statusPublished - 1998 Jan 1

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Pharmacology
    • Organic Chemistry

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  • Cite this

    Yamamoto, Y., Onuki, S., Yumoto, M., & Asao, N. (1998). Radical reaction initiated and stereocontrolled by zinc chloride. Heterocycles, 47(2), 765-780. https://doi.org/10.3987/COM-97-S(N)71