Chiral rare earth metal complex-catalyzed conjugate addition of O-alkylhydroxylamines. An efficient synthetic entry into optically active 2-acyl aziridines

Xiu Lan Jin, Hiroyasu Sugihara, Kazuhiro Daikai, Hiroki Tateishi, Yong Zhi Jin, Hiroshi Furuno, Junji Inanaga

    Research output: Contribution to journalArticlepeer-review

    70 Citations (Scopus)

    Abstract

    The conjugate addition of O-alkylhydroxylamines to α,β-unsaturated ketones is effectively catalyzed by chiral rare earth metal complexes to afford the corresponding β-amino ketones with high enantioselectivities (up to 99% ee) in almost quantitative yields, which are, upon treatment with a base catalyst, quantitatively converted into the 2-acyl aziridines without losing their enantiopurities. The protocol is highly practical thus providing an easy access to enantiopure 2-acyl aziridines and their derivatives in good quantities.

    Original languageEnglish
    Pages (from-to)8321-8329
    Number of pages9
    JournalTetrahedron
    Volume58
    Issue number41
    DOIs
    Publication statusPublished - Oct 7 2002

    All Science Journal Classification (ASJC) codes

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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