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Chiral γ-Amino Amide Synthesis by Heterobimetallic Lanthanum/Lithium/Pybox-Catalyzed Direct Asymmetric Mannich-Type Reactions of α-Keto Anilides†

  1. Gang Lu,
  2. Hiroyuki Morimoto,
  3. Shigeki Matsunaga Dr.,
  4. Masakatsu Shibasaki Prof. Dr.

Article first published online: 24 JUL 2008

DOI: 10.1002/anie.200801564

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 47, Issue 36, pages 6847–6850, August 25, 2008

Additional Information

How to Cite

Lu, G., Morimoto, H., Matsunaga, S. and Shibasaki, M. (2008), Chiral γ-Amino Amide Synthesis by Heterobimetallic Lanthanum/Lithium/Pybox-Catalyzed Direct Asymmetric Mannich-Type Reactions of α-Keto Anilides. Angew. Chem. Int. Ed., 47: 6847–6850. doi: 10.1002/anie.200801564

Author Information

  1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5684-5206 http://www.f.u-tokyo.ac.jp/∼kanai/e_index.html

  1. †

    This work was supported by Grant-in-Aid for Specially Promoted Research, the Sumitomo Foundation, and partially by Grant-in-Aid for Scientific Research on Priority Areas (No. 20037010, Chemistry of Concerto Catalysis). H.M. thanks JSPS Fellowship for Young Scientists. We thank Prof. J. C. Carretero and Dr. R. Gómez Arrayás for their helpful advice on imine synthesis.pybox=pyridine bisoxazoline

Publication History

  1. Issue published online: 20 AUG 2008
  2. Article first published online: 24 JUL 2008
  3. Manuscript Received: 4 APR 2008

Funded by

  • Sumitomo Foundation
  • Grant-in-Aid for Scientific Research. Grant Number: 20037010

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Keywords:

  • amino acids;
  • asymmetric catalysis;
  • asymmetric synthesis;
  • heterometallic complexes;
  • Mannich reaction
Thumbnail image of graphical abstract

Not so Mannich now: A heterobimetallic La/Li/pybox complex was key in direct catalytic asymmetric Mannich-type reactions, using α-keto anilides as synthetic homoenolate equivalents to afford γ-amino amide products in up to >99 % yield, 95 % ee, and >97:3 syn-selectivity. Stereoselective reduction of the α-keto moiety afforded the β-alkyl-γ-amino-α-hydroxy amide with three contiguous stereocenters (PG=protecting group).

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