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Asymmetric Auto-Tandem Catalysis with a Planar-Chiral Ruthenium Complex: Sequential Allylic Amidation and Atom-Transfer Radical Cyclization

Authors

  • Naoya Kanbayashi,

    1. Department of Macromolecular Science, Graduate School of Science, Osaka University, Machikaneyama 1-1, Toyonaka, Osaka 560-0043 (Japan)
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  • Dr. Kazuhiro Takenaka,

    1. The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki, Osaka 567-0047 (Japan)
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  • Dr. Taka-aki Okamura,

    Corresponding author
    1. Department of Macromolecular Science, Graduate School of Science, Osaka University, Machikaneyama 1-1, Toyonaka, Osaka 560-0043 (Japan)
    • Department of Macromolecular Science, Graduate School of Science, Osaka University, Machikaneyama 1-1, Toyonaka, Osaka 560-0043 (Japan)
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  • Prof. Kiyotaka Onitsuka

    Corresponding author
    1. Department of Macromolecular Science, Graduate School of Science, Osaka University, Machikaneyama 1-1, Toyonaka, Osaka 560-0043 (Japan)
    • Department of Macromolecular Science, Graduate School of Science, Osaka University, Machikaneyama 1-1, Toyonaka, Osaka 560-0043 (Japan)
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  • This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology (Japan), and partly by the Sumitomo Foundation and a JSPS Research Fellowship.

Abstract

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Ru does it all: A novel example of an asymmetric auto-tandem reaction catalyzed by a planar-chiral cyclopentadienyl–ruthenium complex is described. The reaction of allylic chloride with α-haloamides provides synthetically useful, diastereomerically and enantiomerically enriched γ-lactams with multiple stereogenic centers through one-pot sequential allylic amidation/atom-transfer radical cyclization. PG=protecting group.

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