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

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  • Masahiko Taniguchi
    Division of Material Chemistry, Faculty of Engineering, Kyoto UniversityYoshida, Sakyo-ku, Kyoto 606-01
  • Koichiro Oshima
    Division of Material Chemistry, Faculty of Engineering, Kyoto UniversityYoshida, Sakyo-ku, Kyoto 606-01
  • Kiitiro Utimoto
    Division of Material Chemistry, Faculty of Engineering, Kyoto UniversityYoshida, Sakyo-ku, Kyoto 606-01

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Abstract

<jats:title>Abstract</jats:title> <jats:p>Stereoselective allylation of 2-formyl amides or 3-oxo amides has been studied. Treatment of 2-formyl-N,N-dimethylpropanamide (1a) with allylzinc bromide gave 3-hydroxy-2,N,N-trimethyl-5-pentenamide as a stereoisomeric mixture (2a : 3a = 63 : 37). Meantime, the reaction of 1a with allyltrimethylsilane in the presence of Lewis acid such as EtAlCl2 or BF3·OEt2 afforded threo-adduct 2a exclusively. Whereas treatment of 2-benzoyl-N,N-dimethylpropanamide (PhCOCH(Me)CONMe2) with allylzinc bromide provided erythro-3-hydroxy-2-methyl-3-phenyl-5-hexenamide with high stereoselectivity, allylation with allylsilane in the presence of a catalytic amount of n-Bu4NF afforded stereoisomeric threo hydroxy amide exclusively.</jats:p>

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