Planar-to-planar chirality transfer in the excited state. Enantiodifferentiating photoisomerization of cyclooctenes sensitized by planar-chiral paracyclophane

Ryo Maeda, Takehiko Wada, Tadashi Mori, Shigeyuki Kono, Nobuhiro Kanomata, Yoshihisa Inoue

    Research output: Contribution to journalArticle

    23 Citations (Scopus)

    Abstract

    Photochemical planar-to-planar chirality transfer was effected by using (R)-[10]paracyclophane-12-carboxylates as a planar-chiral sensitizer and (Z)-cyclooctene and (Z,Z)-1,5-cyclooctadiene as prochiral substrates to give a planar-chiral (E)- and (E,Z)-isomer in up to 44% and 87% enantiomeric excess, respectively, the latter of which being the highest ever reported for a sensitized photochirogenic reaction.

    Original languageEnglish
    Pages (from-to)10379-10381
    Number of pages3
    JournalJournal of the American Chemical Society
    Volume133
    Issue number27
    DOIs
    Publication statusPublished - 2011 Jul 13

    Fingerprint

    Cyclooctanes
    Photoisomerization
    Chirality
    Excited states
    Isomers
    Substrates
    1,5-cyclooctadiene

    ASJC Scopus subject areas

    • Chemistry(all)
    • Catalysis
    • Biochemistry
    • Colloid and Surface Chemistry

    Cite this

    Planar-to-planar chirality transfer in the excited state. Enantiodifferentiating photoisomerization of cyclooctenes sensitized by planar-chiral paracyclophane. / Maeda, Ryo; Wada, Takehiko; Mori, Tadashi; Kono, Shigeyuki; Kanomata, Nobuhiro; Inoue, Yoshihisa.

    In: Journal of the American Chemical Society, Vol. 133, No. 27, 13.07.2011, p. 10379-10381.

    Research output: Contribution to journalArticle

    @article{0752b07edbf74497ae1e4d07757c59c8,
    title = "Planar-to-planar chirality transfer in the excited state. Enantiodifferentiating photoisomerization of cyclooctenes sensitized by planar-chiral paracyclophane",
    abstract = "Photochemical planar-to-planar chirality transfer was effected by using (R)-[10]paracyclophane-12-carboxylates as a planar-chiral sensitizer and (Z)-cyclooctene and (Z,Z)-1,5-cyclooctadiene as prochiral substrates to give a planar-chiral (E)- and (E,Z)-isomer in up to 44{\%} and 87{\%} enantiomeric excess, respectively, the latter of which being the highest ever reported for a sensitized photochirogenic reaction.",
    author = "Ryo Maeda and Takehiko Wada and Tadashi Mori and Shigeyuki Kono and Nobuhiro Kanomata and Yoshihisa Inoue",
    year = "2011",
    month = "7",
    day = "13",
    doi = "10.1021/ja203781f",
    language = "English",
    volume = "133",
    pages = "10379--10381",
    journal = "Journal of the American Chemical Society",
    issn = "0002-7863",
    publisher = "American Chemical Society",
    number = "27",

    }

    TY - JOUR

    T1 - Planar-to-planar chirality transfer in the excited state. Enantiodifferentiating photoisomerization of cyclooctenes sensitized by planar-chiral paracyclophane

    AU - Maeda, Ryo

    AU - Wada, Takehiko

    AU - Mori, Tadashi

    AU - Kono, Shigeyuki

    AU - Kanomata, Nobuhiro

    AU - Inoue, Yoshihisa

    PY - 2011/7/13

    Y1 - 2011/7/13

    N2 - Photochemical planar-to-planar chirality transfer was effected by using (R)-[10]paracyclophane-12-carboxylates as a planar-chiral sensitizer and (Z)-cyclooctene and (Z,Z)-1,5-cyclooctadiene as prochiral substrates to give a planar-chiral (E)- and (E,Z)-isomer in up to 44% and 87% enantiomeric excess, respectively, the latter of which being the highest ever reported for a sensitized photochirogenic reaction.

    AB - Photochemical planar-to-planar chirality transfer was effected by using (R)-[10]paracyclophane-12-carboxylates as a planar-chiral sensitizer and (Z)-cyclooctene and (Z,Z)-1,5-cyclooctadiene as prochiral substrates to give a planar-chiral (E)- and (E,Z)-isomer in up to 44% and 87% enantiomeric excess, respectively, the latter of which being the highest ever reported for a sensitized photochirogenic reaction.

    UR - http://www.scopus.com/inward/record.url?scp=79960054922&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=79960054922&partnerID=8YFLogxK

    U2 - 10.1021/ja203781f

    DO - 10.1021/ja203781f

    M3 - Article

    C2 - 21667983

    AN - SCOPUS:79960054922

    VL - 133

    SP - 10379

    EP - 10381

    JO - Journal of the American Chemical Society

    JF - Journal of the American Chemical Society

    SN - 0002-7863

    IS - 27

    ER -