Communication

Highly Enantio- and Diastereoselective Reactions of γ-Substituted Butenolides Through Direct Vinylogous Conjugate Additions†

  1. Wen Zhang1,‡,
  2. Davin Tan2,‡,
  3. Richmond Lee2,‡,
  4. Guanghu Tong1,
  5. Wenchao Chen1,
  6. Baojian Qi1,
  7. Prof. Dr. Kuo-Wei Huang2,*,
  8. Prof. Dr. Choon-Hong Tan1,3,*,
  9. Prof. Dr. Zhiyong Jiang1,*

Article first published online: 5 SEP 2012

DOI: 10.1002/anie.201205872

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 40, pages 10069–10073, October 1, 2012

Additional Information

How to Cite

Zhang, W., Tan, D., Lee, R., Tong, G., Chen, W., Qi, B., Huang, K.-W., Tan, C.-H. and Jiang, Z. (2012), Highly Enantio- and Diastereoselective Reactions of γ-Substituted Butenolides Through Direct Vinylogous Conjugate Additions . Angew. Chem. Int. Ed., 51: 10069–10073. doi: 10.1002/anie.201205872

Author Information

  1. 1

    Key Laboratory of Natural Medicine and Immune, Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, 475004 (P. R. China)

  2. 2

    King Abdullah University of Science and Technology (KAUST), Division of Chemical and Life Sciences & Engineering, and KAUST Catalysis Center, Thuwal, 23955-6900 (Saudi Arabia)

  3. 3

    Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)

  1. ‡

    These authors contributed equally to this work.

*King Abdullah University of Science and Technology (KAUST), Division of Chemical and Life Sciences & Engineering, and KAUST Catalysis Center, Thuwal, 23955-6900 (Saudi Arabia)

  1. †

    This work was supported by the NSFC (21072044) and the Excellent Youth Foundation of Henan Scientific Committee (114100510003) to Z.J., and by KAUST to K.-W. H.

  2. ‡

    These authors contributed equally to this work.

Publication History

  1. Issue published online: 26 SEP 2012
  2. Article first published online: 5 SEP 2012
  3. Manuscript Received: 24 JUL 2012

Funded by

  • NSFC. Grant Number: 21072044
  • Excellent Youth Foundation of Henan Scientific Committee. Grant Number: 114100510003
  • KAUST

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Keywords:

  • amides;
  • asymmetric catalysis;
  • butenolides;
  • Michael addition;
  • vinylogous conjugate addition
Thumbnail image of graphical abstract

The strength of the weak: An L-tert-leucine-derived amine–thiourea catalyst (see scheme, green box) promotes the asymmetric vinylogous conjugate addition reaction between γ-aryl- and alkyl-substituted butenolides with the butenamides and enoates shown. Computational studies show the preference for the observed stereochemistry is a result of favourable weak non-bonding interactions, which stabilize the transition state.

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