Stereodivergent synthesis of the enolates of a β-amino ester by using lithium N-benzyltrimethylsilylamide

Naoki Asao, Tadao Uyehara, Yoshinori Yamamoto

    Research output: Contribution to journalArticle

    64 Citations (Scopus)

    Abstract

    Highly stereoselective generation of both Z- and E-enolates (1 and 3)2 is accomplished by the conjugate addition of lithium N-benzyltrimethylsilylamide (LSA) to methyl crotonate. The alkylation with alkyl halides and aldol condensation with aldehydes via 1 and 3 are studied. The alkylation of 3 produces moderate to good syn selectivity, while that of 1 gives no selectivity. The aldol condensation of 1 affords the anti-syn isomer (11) predominantly, whereas that of 3 gives the syn-anti isomer (14) preferentially.

    Original languageEnglish
    Pages (from-to)4563-4572
    Number of pages10
    JournalTetrahedron
    Volume46
    Issue number13-14
    DOIs
    Publication statusPublished - 1990

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

    Fingerprint Dive into the research topics of 'Stereodivergent synthesis of the enolates of a β-amino ester by using lithium N-benzyltrimethylsilylamide'. Together they form a unique fingerprint.

  • Cite this