Communication

Catalytic Asymmetric Synthesis of Spirooxindoles by a Mannich-Type Reaction of Isothiocyanato Oxindoles†

  1. Shota Kato1,
  2. Tatsuhiko Yoshino1,
  3. Prof. Dr. Masakatsu Shibasaki3,
  4. Prof. Dr. Motomu Kanai1,2,*,
  5. Dr. Shigeki Matsunaga1,2,*

Article first published online: 4 JUN 2012

DOI: 10.1002/anie.201203005

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 28, pages 7007–7010, July 9, 2012

Additional Information

How to Cite

Kato, S., Yoshino, T., Shibasaki, M., Kanai, M. and Matsunaga, S. (2012), Catalytic Asymmetric Synthesis of Spirooxindoles by a Mannich-Type Reaction of Isothiocyanato Oxindoles . Angew. Chem. Int. Ed., 51: 7007–7010. doi: 10.1002/anie.201203005

Author Information

  1. 1

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

  2. 2

    Kanai Life Science Catalysis Project, ERATO (Japan) Science and Technology Agency, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)

  3. 3

    Institute of Microbial Chemistry, Tokyo Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)

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

  1. †

    This work was supported by ERATO from JST, a Grant-in-Aid for Young Scientists (A) from JSPS, the Naito Foundation, and the Inoue Science Foundation.

Publication History

  1. Issue published online: 4 JUL 2012
  2. Article first published online: 4 JUN 2012
  3. Manuscript Received: 19 APR 2012

Funded by

  • ERATO
  • JSPS
  • Naito Foundation
  • Inoue Science Foundation

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Keywords:

  • asymmetric catalysis;
  • asymmetric synthesis;
  • Mannich reaction;
  • oxindoles;
  • salen
Thumbnail image of graphical abstract

Easy access: A strontium/Schiff base complex as catalyst for the title reaction provided straightforward access to enantiomerically enriched spiro[imidazolidine-4,3′-oxindole] compounds, as well as a spiro[imidazoline-4,3′-oxindole] through a two-step conversion from the Mannich adduct.

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