Short Communication

Asymmetric Allylboration of Aldehydes with Pinacol Allylboronates Catalyzed by 1,1′-Spirobiindane-7,7′-diol (SPINOL) Based Phosphoric Acids

  1. Chun-Hui Xing,
  2. Yuan-Xi Liao,
  3. Yimei Zhang,
  4. Darya Sabarova,
  5. Monica Bassous,
  6. Qiao-Sheng Hu

Article first published online: 16 JAN 2012

DOI: 10.1002/ejoc.201101739

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2012, Issue 6, pages 1115–1118, February 2012

Additional Information

How to Cite

Xing, C.-H., Liao, Y.-X., Zhang, Y., Sabarova, D., Bassous, M. and Hu, Q.-S. (2012), Asymmetric Allylboration of Aldehydes with Pinacol Allylboronates Catalyzed by 1,1′-Spirobiindane-7,7′-diol (SPINOL) Based Phosphoric Acids. Eur. J. Org. Chem., 2012: 1115–1118. doi: 10.1002/ejoc.201101739

Author Information

  1. Department of Chemistry, College of Staten Island and the Graduate Center of the City University of New York, Staten Island, New York 10314, USA, Fax: +1-718-982-3910

Publication History

  1. Issue published online: 13 FEB 2012
  2. Article first published online: 16 JAN 2012
  3. Manuscript Received: 7 DEC 2011

Funded by

  • Professional Staff Congress–City University of New York (PSC–CUNY)

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Keywords:

  • Allylation;
  • Spiro compounds;
  • Phosphorus;
  • Boronates;
  • Aldehydes

Abstract

The asymmetric allylboration of aldehydes with pinacolallylboronates catalyzed by 1,1′-spirobiindane-7,7′-diol (SPINOL) based phosphoric acids is described. 6,6′-Bis(2,4,6-triisopropylphenyl)SPINOL-based phosphoric acid was found to be a general, highly enantioselective catalyst for such allylboration reactions and excellent enantioselectivities were obtained for different types of aldehydes including aromatic aldehydes, α,β-unsaturated aldehydes, propargylic aldehydes, and aliphatic aldehydes.

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