Communication

Brønsted Acid Catalyzed Enantioselective Semipinacol Rearrangement for the Synthesis of Chiral Spiroethers†

  1. Qing-Wei Zhang,
  2. Chun-An Fan Prof. Dr.,
  3. Hai-Jun Zhang,
  4. Yong-Qiang Tu Prof. Dr.,
  5. Yu-Ming Zhao,
  6. Peiming Gu Dr.,
  7. Zhi-Min Chen

Article first published online: 8 OCT 2009

DOI: 10.1002/anie.200904565

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 48, Issue 45, pages 8572–8574, October 26, 2009

Additional Information

How to Cite

Zhang, Q.-W., Fan, C.-A., Zhang, H.-J., Tu, Y.-Q., Zhao, Y.-M., Gu, P. and Chen, Z.-M. (2009), Brønsted Acid Catalyzed Enantioselective Semipinacol Rearrangement for the Synthesis of Chiral Spiroethers. Angew. Chem. Int. Ed., 48: 8572–8574. doi: 10.1002/anie.200904565

Author Information

  1. Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China), Fax: (+86) 931-8912582

  1. †

    This work was supported by the NSFC (Nos. 20621091, 20672048, and 20732002) and the “111” program of MOE. We also thank Prof. Henri B. Kagan (Université de Paris-Sud (XI), France) for helpful discussion.

Publication History

  1. Issue published online: 20 OCT 2009
  2. Article first published online: 8 OCT 2009
  3. Manuscript Received: 16 AUG 2009

Funded by

  • NSFC. Grant Numbers: 20621091, 20672048, 20732002
  • MOE

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Keywords:

  • asymmetric catalysis;
  • Brønsted acids;
  • semipinacols;
  • rearrangements;
  • spirocompounds
Thumbnail image of graphical abstract

A new twist: The catalytic asymmetric semipinacol rearrangement reaction of 2-oxo allylic alcohols 1 in the presence of a catalytic amount of chiral phosphoric acid (R)-2 a or its silver salt (R)-2 b affords enantiomerically pure spiroethers 3.

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