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Communication

Copper-Catalyzed Amination of Ketene Silyl Acetals with Hydroxylamines: Electrophilic Amination Approach to α-Amino Acids†

  1. Naoki Matsuda,
  2. Dr. Koji Hirano*,
  3. Prof. Dr. Tetsuya Satoh,
  4. Prof. Dr. Masahiro Miura*

Article first published online: 15 OCT 2012

DOI: 10.1002/anie.201206755

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 47, pages 11827–11831, November 19, 2012

Additional Information

How to Cite

Matsuda, N., Hirano, K., Satoh, T. and Miura, M. (2012), Copper-Catalyzed Amination of Ketene Silyl Acetals with Hydroxylamines: Electrophilic Amination Approach to α-Amino Acids . Angew. Chem. Int. Ed., 51: 11827–11831. doi: 10.1002/anie.201206755

Author Information

  1. Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan)

*Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan)

  1. †

    This work was partly supported by Grants-in-Aid from the MEXT and JSPS (Japan).

Publication History

  1. Issue published online: 14 NOV 2012
  2. Article first published online: 15 OCT 2012
  3. Manuscript Received: 21 AUG 2012

Funded by

  • MEXT
  • JSPS (Japan)

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Keywords:

  • amination;
  • amino acids;
  • copper;
  • synthetic methods;
  • umpolung
Thumbnail image of graphical abstract

Role reversal: The title reaction has been developed to deliver α-amino acids under very mild reaction conditions (see scheme; dpppen=1,5-bis(diphenylphosphino)pentane). The catalysis provides a new C[BOND]N bond-forming approach for the synthesis of α-amino acids by using an umpolung, electrophilic amination strategy.

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