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Asymmetric Michael Addition Reaction of 3-Substituted Oxindoles to Nitroolefins Catalyzed by a Chiral Alkyl- Substituted Thiourea Catalyst

  1. Xin Li1,
  2. Bo Zhang2,
  3. Zhi-Guo Xi2,
  4. Sanzhong Luo1,
  5. Jin-Pei Cheng1,2

Article first published online: 12 JAN 2010

DOI: 10.1002/adsc.200900630

Issue

Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

Volume 352, Issue 2-3, pages 416–424, February 15, 2010

Additional Information

How to Cite

Li, X., Zhang, B., Xi, Z.-G., Luo, S. and Cheng, J.-P. (2010), Asymmetric Michael Addition Reaction of 3-Substituted Oxindoles to Nitroolefins Catalyzed by a Chiral Alkyl- Substituted Thiourea Catalyst. Adv. Synth. Catal., 352: 416–424. doi: 10.1002/adsc.200900630

Author Information

  1. 1

    Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function , Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, People's Republic of China, Fax: (+86)-10-6255-4449

  2. 2

    Department of Chemistry and State Key Laboratory of Elementoorganic Chemistry, Nankai University, Tianjin 300071, People's Republic of China

Publication History

  1. Issue published online: 17 FEB 2010
  2. Article first published online: 12 JAN 2010
  3. Manuscript Revised: 15 NOV 2009
  4. Manuscript Received: 11 SEP 2009

Funded by

  • Natural Science Foundation. Grant Numbers: 20632060, 20702052, 20902091
  • MOST. Grant Numbers: 2008CB617501, 2009ZX09501-018

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Keywords:

  • bifunctional thioureas;
  • Michael addition reaction;
  • nitroolefins;
  • organocatalysis;
  • oxindoles

Abstract

A simple alkylthiourea was found to be an effective catalyst for the Michael addition reaction of 3-substituted oxindole to nitroolefins. A number of 3,3′-substituted oxindole derivatives, which have two vicinal quaternary-tertiary chiral centers were synthesized with up to 99% yield, 19:1 dr and 98% ee.

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