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Stereoselective One-Pot Synthesis of 1-Aminoindanes and 5,6-Fused Azacycles Using a Gold-Catalyzed Redox-Pinacol-Mannich-Michael Cascade†

  1. Hyun-Suk Yeom1,
  2. Youngun Lee1,
  3. Jaewon Jeong1,
  4. Eunsoo So1,
  5. Soojin Hwang1,
  6. Ji-Eun Lee Dr.2,
  7. Shim Sung Lee Prof. Dr.2,
  8. Seunghoon Shin Prof. Dr.1

Article first published online: 27 JAN 2010

DOI: 10.1002/anie.200906346

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 49, Issue 9, pages 1611–1614, February 22, 2010

Additional Information

How to Cite

Yeom, H.-S., Lee, Y., Jeong, J., So, E., Hwang, S., Lee, J.-E., Lee, S. and Shin, S. (2010), Stereoselective One-Pot Synthesis of 1-Aminoindanes and 5,6-Fused Azacycles Using a Gold-Catalyzed Redox-Pinacol-Mannich-Michael Cascade. Angew. Chem. Int. Ed., 49: 1611–1614. doi: 10.1002/anie.200906346

Author Information

  1. 1

    Department of Chemistry and Research Institute for Natural Sciences, Hanyang University, Seoul 133-791 (Korea), Fax: (+82) 2-2299-0762

  2. 2

    Department of Chemistry, Gyeongsang National University, Chinju 660-701 (Korea)

  1. †

    This work was supported by the National Research Foundation of Korea (KRF-2009-000-0000-0803). H.S.Y., Y.L., J.J., and E.S. thank the BK21 program for the financial support. H.S.Y. also thanks the Seoul Science Foundation for a fellowship.

Publication History

  1. Issue published online: 17 FEB 2010
  2. Article first published online: 27 JAN 2010
  3. Manuscript Received: 11 NOV 2009

Funded by

  • National Research Foundation of Korea. Grant Number: KRF-2009-000-0000-0803
  • BK21 program
  • Seoul Science Foundation

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Keywords:

  • carbenoids;
  • cascade reactions;
  • gold;
  • Mannich reactions;
  • redox chemistry
Thumbnail image of graphical abstract

Just another Mannich Monday: A cascade intramolecular redox-pinacol-Mannich-Michael reaction sequence catalyzed by gold complexes can be used to generate a variety of structures including spirocycles, 1-aminoindanes, and 5,6-fused azabicycles that have a quaternary carbon center. The reaction is characterized by complete atom-economy, high diastereoselectivity, and remarkable efficiency through tandem reactions.

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