Asymmetric catalysis with self-organized chiral lanthanum complexes: Practical and highly enantioselective epoxidation of α,β-unsaturated ketones

Kazuhiro Daikai, Tetsuji Hayano, Rie Kino, Hiroshi Furuno, Takumi Kagawa, Junji Inanaga

    Research output: Contribution to journalArticlepeer-review

    34 Citations (Scopus)

    Abstract

    A highly efficient and practical method for obtaining α,β-epoxy ketones with high optical purities was developed. The chiral lanthanum complex self-organized in situ from lanthanum triisopropoxide, (R)-BINOL, triarylphosphine oxide, and alkyl hydroperoxide (1:1:1:1) was found to catalyze the epoxidation of α,β-unsaturated ketones with tert-butyl hydroperoxide or cumene hydroperoxide at room temperature to give the corresponding epoxy ketones in high enantioselectivities (up to >99% enantiomeric excess (ee)). A remarkably high asymmetric amplification, a positive nonlinear effect, was observed in the epoxidation of chalcone, which strongly suggests the formation of a dinuclear peroxide-involved p-complex as the active catalyst.

    Original languageEnglish
    Pages (from-to)83-88
    Number of pages6
    JournalChirality
    Volume15
    Issue number1
    DOIs
    Publication statusPublished - Jan 7 2003

    All Science Journal Classification (ASJC) codes

    • Analytical Chemistry
    • Catalysis
    • Pharmacology
    • Drug Discovery
    • Spectroscopy
    • Organic Chemistry

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