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Iron-Catalyst-Switched Selective Conjugate Addition of Grignard Reagents: α,β,γ,δ-Unsaturated Amides as Versatile Templates for Asymmetric Three-Component Coupling Processes†

  1. Satoshi Okada‡,
  2. Kyohei Arayama‡,
  3. Ryuji Murayama,
  4. Takumi Ishizuka,
  5. Keiichi Hara,
  6. Naoki Hirone,
  7. Takeshi Hata Dr.,
  8. Hirokazu Urabe Prof. Dr.

Article first published online: 29 JUL 2008

DOI: 10.1002/anie.200801928

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 47, Issue 36, pages 6860–6864, August 25, 2008

Additional Information

How to Cite

Okada, S., Arayama, K., Murayama, R., Ishizuka, T., Hara, K., Hirone, N., Hata, T. and Urabe, H. (2008), Iron-Catalyst-Switched Selective Conjugate Addition of Grignard Reagents: α,β,γ,δ-Unsaturated Amides as Versatile Templates for Asymmetric Three-Component Coupling Processes. Angew. Chem. Int. Ed., 47: 6860–6864. doi: 10.1002/anie.200801928

Author Information

  1. Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-59 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501 (Japan), Fax: (+81) 45-924-5849 http://www.urabe-lab.bio.titech.ac.jp

  1. ‡

    These authors contributed equally to this work.

  1. †

    This work was supported by a Grant-in-Aid for Scientific Research on Priority Area (No.16073208) and a Grant-in-Aid for Young Scientists (B) (No. 20750071, to T.H.) from the Ministry of Education, Culture, Sports, Science and Technology (Japan).

Publication History

  1. Issue published online: 20 AUG 2008
  2. Article first published online: 29 JUL 2008
  3. Manuscript Received: 24 APR 2008

Funded by

  • Grant-in-Aid for Scientific Research on Priority Area. Grant Number: 16073208
  • Grant-in-Aid for Young Scientists (B). Grant Number: 20750071
  • Ministry of Education, Culture, Sports, Science and Technology (Japan)

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Keywords:

  • amides;
  • asymmetric reaction;
  • conjugate addition;
  • Grignard reagents;
  • iron
Thumbnail image of graphical abstract

Diene for conjugate addition: Iron(II) chloride switches the reaction course of the three-component coupling of a Grignard reagent, an alkyl halide, and a dienamide, thus making the amide a simple yet versatile chiral template.

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