Syn selective vinylogous mukaiyama aldol reaction using Z,EVinylketene N,O-acetal with acetals

Naoya Sagawa, Hiroki Moriya, Seijiro Hosokawa

    Research output: Contribution to journalArticle

    9 Citations (Scopus)

    Abstract

    Stereoselective vinylogous Mukaiyama aldol reactions using the Z,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary, derived from (E)-3-pentenoic acid and Lvaline, have been achieved. The reaction proceeded smoothly to give a syn adduct in high stereoselectivity. Since the products possess structures including δ-alkoxy-γ-methyl-α,β-unsaturated imide, this reaction would be applicable to synthesize polyketides in a short procedure.

    Original languageEnglish
    Pages (from-to)250-253
    Number of pages4
    JournalOrganic Letters
    Volume19
    Issue number1
    DOIs
    Publication statusPublished - 2017 Jan 1

    Fingerprint

    Imides
    Polyketides
    Stereoselectivity
    acetals
    Acetals
    Acids
    imides
    adducts
    acids
    products
    alkoxyl radical
    3-hydroxybutanal

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

    Cite this

    Syn selective vinylogous mukaiyama aldol reaction using Z,EVinylketene N,O-acetal with acetals. / Sagawa, Naoya; Moriya, Hiroki; Hosokawa, Seijiro.

    In: Organic Letters, Vol. 19, No. 1, 01.01.2017, p. 250-253.

    Research output: Contribution to journalArticle

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