Syn-selective kobayashi aldol reaction using acetals

Hiroyuki Tsukada, Yuki Mukaeda, Seijiro Hosokawa

    Research output: Contribution to journalArticle

    23 Citations (Scopus)

    Abstract

    The Kobayashi aldol reaction has been used to construct anti-aldol products by remote stereoinduction. Since the product of the Kobayashi aldol reaction has a typical polyketide structure, this reaction has been applied to the total synthesis of natural products. By varying this reaction, it was found that the reaction with acetals in the presence of Lewis acid proceeded to give syn adducts in high stereoselectivity. This is the first example of the stereoselective reaction of the chiral dienol ether and acetals.

    Original languageEnglish
    Pages (from-to)678-681
    Number of pages4
    JournalOrganic Letters
    Volume15
    Issue number3
    DOIs
    Publication statusPublished - 2013 Feb 1

    Fingerprint

    acetals
    Acetals
    Polyketides
    Stereoselectivity
    Lewis Acids
    Biological Products
    Ether
    products
    adducts
    3-hydroxybutanal
    ethers
    acids
    synthesis

    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Biochemistry

    Cite this

    Syn-selective kobayashi aldol reaction using acetals. / Tsukada, Hiroyuki; Mukaeda, Yuki; Hosokawa, Seijiro.

    In: Organic Letters, Vol. 15, No. 3, 01.02.2013, p. 678-681.

    Research output: Contribution to journalArticle

    Tsukada, Hiroyuki ; Mukaeda, Yuki ; Hosokawa, Seijiro. / Syn-selective kobayashi aldol reaction using acetals. In: Organic Letters. 2013 ; Vol. 15, No. 3. pp. 678-681.
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