Stereoselective Allylation of 2-Formyl Amides or 3-Oxo Amides

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Author(s)

    • OSHIMA Koichiro
    • Division of Material Chemistry, Faculty of Engineering, Kyoto University
    • UTIMOTO Kiitiro
    • Division of Material Chemistry, Faculty of Engineering, Kyoto University

Abstract

Stereoselective allylation of 2-formyl amides or 3-oxo amides has been studied. Treatment of 2-formyl-<i>N</i>,<i>N</i>-dimethylpropanamide (<b>1a</b>) with allylzinc bromide gave 3-hydroxy-2,<i>N</i>,<i>N</i>-trimethyl-5-pentenamide as a stereoisomeric mixture (<b>2a</b> : <b>3a</b> = 63 : 37). Meantime, the reaction of <b>1a</b> with allyltrimethylsilane in the presence of Lewis acid such as EtAlCl<sub>2</sub> or BF<sub>3</sub>·OEt<sub>2</sub> afforded <i>threo</i>-adduct <b>2a</b> exclusively. Whereas treatment of 2-benzoyl-<i>N</i>,<i>N</i>-dimethylpropanamide (PhCOCH(Me)CONMe<sub>2</sub>) with allylzinc bromide provided <i>erythro</i>-3-hydroxy-2-methyl-3-phenyl-5-hexenamide with high stereoselectivity, allylation with allylsilane in the presence of a catalytic amount of <i>n</i>-Bu<sub>4</sub>NF afforded stereoisomeric <i>threo</i> hydroxy amide exclusively.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 68(2), 645-653, 1995-02-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008886664
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • Data Source
    CJP  J-STAGE 
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