Reversal in enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator

Takanori Shibata, Hikaru Tarumi, Tsuneomi Kawasaki, Kenso Soai

    Research output: Contribution to journal › Article

    9 Citations (Scopus)

    Abstract

    A reversal in enantioselectivity was observed by the combination of a chiral diol and achiral alcohols as a chiral initiator in the asymmetric alkylation of a pyrimidine-5-carbaldehyde using diisopropylzinc. (2S,3S)-Butane-2,3-diol alone induced (R)-pyrimidyl alkanol, while a mixture of the chiral diol and phenol derivatives induced (S)-pyrimidyl alkanol. The effect of achiral alcohols is also discussed.

    Original languageEnglish
    Pages (from-to)1023-1027
    Number of pages5
    JournalTetrahedron Asymmetry
    Volume23
    Issue number14
    DOIs
    Publication statusPublished - 2012 Jul 31

    Fingerprint

    autocatalysis
    Enantioselectivity
    initiators
    alcohols
    Alcohols
    alkylation
    Alkylation
    Butane
    pyrimidines
    butanes
    Phenol
    phenols
    Phenols
    Derivatives
    butane
    pyrimidine

    ASJC Scopus subject areas

    • Organic Chemistry
    • Inorganic Chemistry
    • Physical and Theoretical Chemistry
    • Catalysis

    Cite this

    Reversal in enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator. / Shibata, Takanori; Tarumi, Hikaru; Kawasaki, Tsuneomi; Soai, Kenso.

    In: Tetrahedron Asymmetry, Vol. 23, No. 14, 31.07.2012, p. 1023-1027.

    Research output: Contribution to journal › Article

    Shibata, T, Tarumi, H, Kawasaki, T & Soai, K 2012, 'Reversal in enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator', Tetrahedron Asymmetry, vol. 23, no. 14, pp. 1023-1027. https://doi.org/10.1016/j.tetasy.2012.07.010
    Shibata T, Tarumi H, Kawasaki T, Soai K. Reversal in enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator. Tetrahedron Asymmetry. 2012 Jul 31;23(14):1023-1027. https://doi.org/10.1016/j.tetasy.2012.07.010
    Shibata, Takanori ; Tarumi, Hikaru ; Kawasaki, Tsuneomi ; Soai, Kenso. / Reversal in enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator. In: Tetrahedron Asymmetry. 2012 ; Vol. 23, No. 14. pp. 1023-1027.
    @article{5b795634811d4fdc94d19da5e159a49e,
    title = "Reversal in enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator",
    abstract = "A reversal in enantioselectivity was observed by the combination of a chiral diol and achiral alcohols as a chiral initiator in the asymmetric alkylation of a pyrimidine-5-carbaldehyde using diisopropylzinc. (2S,3S)-Butane-2,3-diol alone induced (R)-pyrimidyl alkanol, while a mixture of the chiral diol and phenol derivatives induced (S)-pyrimidyl alkanol. The effect of achiral alcohols is also discussed.",
    author = "Takanori Shibata and Hikaru Tarumi and Tsuneomi Kawasaki and Kenso Soai",
    year = "2012",
    month = "7",
    day = "31",
    doi = "10.1016/j.tetasy.2012.07.010",
    language = "English",
    volume = "23",
    pages = "1023--1027",
    journal = "Tetrahedron Asymmetry",
    issn = "0957-4166",
    publisher = "Elsevier Limited",
    number = "14",

    }

    TY - JOUR

    T1 - Reversal in enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator

    AU - Shibata, Takanori

    AU - Tarumi, Hikaru

    AU - Kawasaki, Tsuneomi

    AU - Soai, Kenso

    PY - 2012/7/31

    Y1 - 2012/7/31

    N2 - A reversal in enantioselectivity was observed by the combination of a chiral diol and achiral alcohols as a chiral initiator in the asymmetric alkylation of a pyrimidine-5-carbaldehyde using diisopropylzinc. (2S,3S)-Butane-2,3-diol alone induced (R)-pyrimidyl alkanol, while a mixture of the chiral diol and phenol derivatives induced (S)-pyrimidyl alkanol. The effect of achiral alcohols is also discussed.

    AB - A reversal in enantioselectivity was observed by the combination of a chiral diol and achiral alcohols as a chiral initiator in the asymmetric alkylation of a pyrimidine-5-carbaldehyde using diisopropylzinc. (2S,3S)-Butane-2,3-diol alone induced (R)-pyrimidyl alkanol, while a mixture of the chiral diol and phenol derivatives induced (S)-pyrimidyl alkanol. The effect of achiral alcohols is also discussed.

    UR - http://www.scopus.com/inward/record.url?scp=84865499251&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=84865499251&partnerID=8YFLogxK

    U2 - 10.1016/j.tetasy.2012.07.010

    DO - 10.1016/j.tetasy.2012.07.010

    M3 - Article

    VL - 23

    SP - 1023

    EP - 1027

    JO - Tetrahedron Asymmetry

    JF - Tetrahedron Asymmetry

    SN - 0957-4166

    IS - 14

    ER -

    Access to Document