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

Naoki Asao, Tadao Uyehara, Yoshinori Yamamoto

    Research output: Contribution to journalArticlepeer-review

    54 Citations (Scopus)

    Abstract

    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.

    Original languageEnglish
    Pages (from-to)4173-4180
    Number of pages8
    JournalTetrahedron
    Volume44
    Issue number13
    DOIs
    Publication statusPublished - 1988 Jan 1

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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