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

    研究成果: Review article

    4 引用 (Scopus)

    抄録

    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.

    元の言語English
    ページ(範囲)831-849
    ページ数19
    ジャーナルYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
    75
    発行部数8
    出版物ステータスPublished - 2017

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    Acetals
    Biological Products
    Carbon
    3-hydroxybutanal
    ketene

    ASJC Scopus subject areas

    • Organic Chemistry

    これを引用

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    title = "Remote asymmetric induction reactions and wide range stereocontrol strategy for synthesis of polypropionates",
    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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    AB - 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.

    KW - Acylation

    KW - Alkylation

    KW - Bromination

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    KW - Total synthesis

    KW - Vinylogous mukaiyama aldol reaction

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