Lithium n-benzyltrimethylsilylamide (LSA): a new reagent for conjugate addition - enolate trapping reactions

Naoki Asao, Tadao Uyehara, Yoshinori Yamamoto

    研究成果: Article査読

    54 被引用数 (Scopus)

    抄録

    Lithium N-benzyltrimethylsilyl amide (LSA) adds to crotonates in a 1,4-manner, though the reaction of ordinary lithium amides with α,β-unsaturated carbonyl compounds is accompanied with a 1,2-addition and hydrogen abstraction at the γ-position. The conjugate addition via LSA followed by enolate trapping with electrophiles produces the corresponding α-substituted β-amino esters, which are, in turn, converted into β-lactams and α-substituted α, β-unsaturated esters.

    本文言語English
    ページ(範囲)4173-4180
    ページ数8
    ジャーナルTetrahedron
    44
    13
    DOI
    出版ステータスPublished - 1988 1 1

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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