Radical reaction initiated and stereocontrolled by zinc chloride

Yoshinori Yamamoto, Setsuko Onuki, Masatoshi Yumoto, Naoki Asao

    研究成果: Article査読

    9 被引用数 (Scopus)

    抄録

    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.

    本文言語English
    ページ(範囲)765-780
    ページ数16
    ジャーナルHeterocycles
    47
    2
    DOI
    出版ステータスPublished - 1998 1 1

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Pharmacology
    • Organic Chemistry

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