Catalytic conversion of conjugated enones into optically active α-keto aziridines using chiral rare earth metal complexes

Hiroyasu Sugihara, Kazuhiro Daikai, Xiu Lan Jin, Hiroshi Furuno, Junji Inanaga

    Research output: Contribution to journalArticlepeer-review

    48 Citations (Scopus)

    Abstract

    Optically active N-unsubstituted α-keto aziridines 2 were synthesized from conjugated enones 1 via the Sc[(R)-BNP]3-catalyzed enantioselective Michael addition of O-methylhydroxylamine followed by the La(O-i-Pr)3-catalyzed ring closure of the corresponding β-methoxyamino ketones 3. A remarkably high asymmetric amplification was observed during the Michael addition, and notable kinetic resolution was also realized during the ring closure reaction when a La(O-i-Pr)3-(R)-BINOL catalyst system was employed.

    Original languageEnglish
    Pages (from-to)2735-2739
    Number of pages5
    JournalTetrahedron Letters
    Volume43
    Issue number15
    DOIs
    Publication statusPublished - Apr 8 2002

    All Science Journal Classification (ASJC) codes

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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