Communication

Asymmetric Catalysis: Resin-Bound Hydroxyprolylthreonine Derivatives in Enamine-Mediated Reactions†

  1. Richard D. Carpenter1,
  2. James C. Fettinger Dr.1,
  3. Kit S. Lam Prof.2,
  4. Mark J. Kurth Prof.1

Article first published online: 15 JUL 2008

DOI: 10.1002/anie.200801811

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 47, Issue 34, pages 6407–6410, August 11, 2008

Additional Information

How to Cite

Carpenter, R., Fettinger, J., Lam, K. and Kurth, M. (2008), Asymmetric Catalysis: Resin-Bound Hydroxyprolylthreonine Derivatives in Enamine-Mediated Reactions. Angewandte Chemie International Edition, 47: 6407–6410. doi: 10.1002/anie.200801811

Author Information

  1. 1

    Department of Chemistry, University of California-Davis, Davis, CA 95616 (USA), Fax: (+1) 530-752-8895 http://chemgroups.ucdavis.edu/∼kurth/index.htm

  2. 2

    Division of Hematology/Oncology,Department of Internal Medicine, University of California-Davis Cancer Center, Sacramento, CA 95817 (USA)

  1. †

    This work was supported by the National Science Foundation (NSF; CHE-0614756) and the National Institute for General Medical Sciences (GM076151). NMR spectrometers used in this work were funded in part by the NSF (CHE-0443516 and CHE-9808183). RDC thanks the American Chemical Society's Division of Medicinal Chemistry for Predoctoral Fellowship support (sponsored by Sanofi-Aventis), the Howard Hughes Medical Institute for their Med into Grad Fellowship, and UC Davis for their R. Bryan Miller Graduate Fellowship.

Publication History

  1. Issue published online: 4 AUG 2008
  2. Article first published online: 15 JUL 2008
  3. Manuscript Received: 17 APR 2008

Funded by

  • National Science Foundation (NSF. Grant Number: CHE-0614756
  • National Institute for General Medical Sciences. Grant Numbers: GM076151, CHE-0443516, CHE-9808183
  • Howard Hughes Medical Institute

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Keywords:

  • asymmetric catalysis;
  • heterocycles;
  • heterogeneous catalysis;
  • solid-phase synthesis;
  • stereoselectivity

Graphical Abstract

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Control of stereochemistry is achieved using two TentaGel-bound di-tert-butoxy-protected hydroxyprolyl-threonine catalysts (see picture, sphere represents TentaGel). These catalysts mediate asymmetric tandem enamine/Michael reactions with high enantioselectivity and complete diastereoselectivity; the choice of catalyst depends on the desired absolute configuration.

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