Remote asymmetric induction reactions and wide range stereocontrol strategy for synthesis of polypropionates

    Research output: Contribution to journalReview article

    4 Citations (Scopus)

    Abstract

    In 2004 we reported an anti-selective remote asymmetric induction reaction using chiral vinyl- ketene silyl Ar,Oacetal 1 (the stereoselective vinylogous Mukaiyama aldol reaction). The reaction has been applied to natural product synthesis by many groups since the reaction makes syntheses short and efficient by simultaneous introduction of both asymmetric centers and the multiply functionalized carbon chain. Recently, we have developed a variety of remote asymmetric induction reactions using the £.£-vinylketene Ar,0-Acetal 1. Additionally, we have developed a new strategy to synthesize polypropionates in short steps by combining remote asymmetric induction reactions and functionalization of double bonds. In this paper, the new strategy as well as new remote asymmetric induction reactions and their applications to syntheses of polypropionates are described.

    Original languageEnglish
    Pages (from-to)831-849
    Number of pages19
    JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
    Volume75
    Issue number8
    Publication statusPublished - 2017

    Fingerprint

    Acetals
    Biological Products
    Carbon
    3-hydroxybutanal
    ketene

    Keywords

    • Acylation
    • Alkylation
    • Bromination
    • Polyketide library
    • Polypropionate
    • Remote asymmetric induction
    • Total synthesis
    • Vinylogous mukaiyama aldol reaction

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

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    abstract = "In 2004 we reported an anti-selective remote asymmetric induction reaction using chiral vinyl- ketene silyl Ar,Oacetal 1 (the stereoselective vinylogous Mukaiyama aldol reaction). The reaction has been applied to natural product synthesis by many groups since the reaction makes syntheses short and efficient by simultaneous introduction of both asymmetric centers and the multiply functionalized carbon chain. Recently, we have developed a variety of remote asymmetric induction reactions using the £.£-vinylketene Ar,0-Acetal 1. Additionally, we have developed a new strategy to synthesize polypropionates in short steps by combining remote asymmetric induction reactions and functionalization of double bonds. In this paper, the new strategy as well as new remote asymmetric induction reactions and their applications to syntheses of polypropionates are described.",
    keywords = "Acylation, Alkylation, Bromination, Polyketide library, Polypropionate, Remote asymmetric induction, Total synthesis, Vinylogous mukaiyama aldol reaction",
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