Communication

Incorporation of Peptide Isosteres into Enantioselective Peptide-Based Catalysts as Mechanistic Probes

  1. Melissa M. Vasbinder,
  2. Elizabeth R. Jarvo,
  3. Scott J. Miller Prof.

Article first published online: 2 AUG 2001

DOI: 10.1002/1521-3773(20010803)40:15<2824::AID-ANIE2824>3.0.CO;2-J

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 40, Issue 15, pages 2824–2827, August 3, 2001

Additional Information

How to Cite

Vasbinder, M. M., Jarvo, E. R. and Miller, S. J. (2001), Incorporation of Peptide Isosteres into Enantioselective Peptide-Based Catalysts as Mechanistic Probes . Angewandte Chemie International Edition, 40: 2824–2827. doi: 10.1002/1521-3773(20010803)40:15<2824::AID-ANIE2824>3.0.CO;2-J

Author Information

  1. Department of Chemistry, Boston College Chestnut Hill, MA 02467-3860 (USA) Fax: (+1) 617-552-3620

Publication History

  1. Issue published online: 2 AUG 2001
  2. Article first published online: 2 AUG 2001
  3. Manuscript Received: 21 MAR 2001

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Keywords:

  • asymmetric catalysis;
  • kinetic resolution;
  • peptidomimetics;
  • reaction mechanisms

Graphical Abstract

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Olefinic analogues of effective peptide-based catalysts for the kinetic resolution of functionalized racemic secondary alcohols have been synthesized. The isosteric replacement of the peptide amide bond in 1 with an (E)-alkene to form 2 has enabled the evaluation of the kinetic role of particular amides within these catalysts.

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