Highly enantioselective homogeneous catalysis of chiral rare earth phosphates in the hetero-Diels-Alder reaction

Hiroshi Furuno, Takeshi Kambara, Yumiko Tanaka, Takeshi Hanamoto, Takumi Kagawa, Junji Inanaga

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    52 Citations (Scopus)

    Abstract

    Two types of novel rare earth (RE) complexes were synthesized and used as a chiral Lewis acid catalyst for the hetero-Diels-Alder reaction of carbonyl compounds with the Danishefsky's diene under homogeneous conditions. The Y[(R)-H8-BNP]3 (3-Y)-catalyzed reaction of aromatic aldehydes and the Yb[(R)-BNP]3 (1-Yb)-catalyzed reaction of phenylglyoxylates afforded the corresponding cycloadducts with excellent optical purities (up to 99% ee) in high yields at room temperature. The successful recycling uses of the scandium catalyst (3-Sc) are also described.

    Original languageEnglish
    Pages (from-to)6129-6132
    Number of pages4
    JournalTetrahedron Letters
    Volume44
    Issue number32
    DOIs
    Publication statusPublished - Aug 4 2003

    All Science Journal Classification (ASJC) codes

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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