Stereoselective Tandem Aldol-Tishchenko Reaction with Acylsilanes

DOI DOI PDF 被引用文献3件 参考文献32件
  • Mitsunori Honda
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Ryota Iwamoto
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Yoshie Nogami
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Masahito Segi
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University

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<jats:title>Abstract</jats:title> <jats:p>The treatment of acetyltrimethylsilane with LDA, followed by reaction of the resulting enolate with the excess amount of aldehydes gave the corresponding 1,3-diol derivatives in moderate yields with perfect diastereoselectivity as a single regioisomer via tandem aldol-Tishchenko reaction, whereas the reaction with α-branched aldehydes under similar conditions gives a mixture of two regioisomers. The reaction using benzyl trimethylsilyl ketone afforded the corresponding 1,3-diol monoesters having three contiguous stereogenic centers with perfect levels of stereochemical control in one-pot.</jats:p>

収録刊行物

  • Chemistry Letters

    Chemistry Letters 34 (4), 466-467, 2005-02-26

    Oxford University Press (OUP)

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