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Highly Enantio- and Diastereoselective Generation of Two Quaternary Centers in Spirocyclopropanation of Oxindole Derivatives.

  1. Artur Noole1,2,
  2. Natalia S. Sucman3,
  3. Dr. Mikhail A. Kabeshov1,
  4. Prof. Dr. Tõnis Kanger2,
  5. Prof. Dr. Fliur Z. Macaev3,
  6. Prof. Dr. Andrei V. Malkov1,*

Article first published online: 30 OCT 2012

DOI: 10.1002/chem.201203099

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 18, Issue 47, pages 14929–14933, November 19, 2012

Additional Information

How to Cite

Noole, A., Sucman, N. S., Kabeshov, M. A., Kanger, T., Macaev, F. Z. and Malkov, A. V. (2012), Highly Enantio- and Diastereoselective Generation of Two Quaternary Centers in Spirocyclopropanation of Oxindole Derivatives. Chem. Eur. J., 18: 14929–14933. doi: 10.1002/chem.201203099

Author Information

  1. 1

    Department of Chemistry, Loughborough University, Loughborough LE11 3TU (UK), Fax: (+44) 1509-223925

  2. 2

    Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, Tallinn 12618 (Estonia)

  3. 3

    Institute of Chemistry, Academiei str. 3, Chisinau 2028 (Moldova)

*Department of Chemistry, Loughborough University, Loughborough LE11 3TU (UK), Fax: (+44) 1509-223925

Publication History

  1. Issue published online: 13 NOV 2012
  2. Article first published online: 30 OCT 2012
  3. Manuscript Received: 31 AUG 2012

Funded by

  • RSC. Grant Number: JP090309
  • COST-ORCA. Grant Number: CM0905

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Keywords:

  • asymmetric catalysis;
  • cascade reactions;
  • cyclization;
  • organocatalysis;
  • spiro compounds
Thumbnail image of graphical abstract

Spirocyclopropanes: Only one out of eight possible stereoisomers was obtained in the asymmetric cascade cyclopropanation of alkylidene oxindoles with ethyl 2-chloroacetoacetate. Improved catalyst design ensured that spirocyclopropyl oxindoles featuring two quaternary centers were synthesized in high yield and high enantio- and diastereoselectivity (see scheme).

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