Short Communication

Synthesis of Novel Functionalized Polymers for the Diastereoselective Protonation of Chiral Enolates

  1. Marc Mackenstedt,
  2. Norbert Krause

Article first published online: 2 NOV 2004

DOI: 10.1002/ejoc.200400429

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2004, Issue 22, pages 4531–4534, November 2004

Additional Information

How to Cite

Mackenstedt, M. and Krause, N. (2004), Synthesis of Novel Functionalized Polymers for the Diastereoselective Protonation of Chiral Enolates. European Journal of Organic Chemistry, 2004: 4531–4534. doi: 10.1002/ejoc.200400429

Author Information

  1. Organic Chemistry II, University of Dortmund, 44221 Dortmund, Germany, Fax: +49 231/755-3884

Publication History

  1. Issue published online: 2 NOV 2004
  2. Article first published online: 2 NOV 2004
  3. Manuscript Received: 18 JUN 2004

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Keywords:

  • Chelation;
  • Chiral enolates;
  • Diastereoselectivity;
  • Functionalized polymers;
  • Protonations

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Abstract

The polymeric, chelating proton donors 7 and 8 were synthesized by radical polymerization of the monomers 5/6 with different amounts of styrene. Protonation of chiral lithium enolates derived from silyl enol ethers 9 gave cis/trans ratios of up to 94:6 (10a) and 99:1 (10b), respectively. The polymers can be recycled and used repeatedly without appreciable loss of selectivity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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