Highly stereodivergent generation of the Z- and E-enolates of a β-amino ester via conjugate addition to methyl crotonate by using lithium N-benzyltrimethylsilylamide as a nitrogen nucleophile, and application to stereoselective aldol reactions

Tadao Uyehara, Naoki Asao, Yoshinori Yamamoto

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    31 Citations (Scopus)

    Abstract

    Methods for highly stereoselective generation of both Z- and E-enolates of a β-amino ester have been developed on the basis of a conjugate addition of lithium N-benzyltrimethylsilylamide to methyl crotonate and applied to stereoselective synthesis of anti,syn- and syn,anti-β-amino-β′- hydroxy esters by treatment with aldehyde.

    Original languageEnglish
    Pages (from-to)753-754
    Number of pages2
    JournalJournal of the Chemical Society, Chemical Communications
    Issue number12
    DOIs
    Publication statusPublished - 1989 Jan 1

    ASJC Scopus subject areas

    • Molecular Medicine

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