Effect of Ligand Structure on the Zinc-Catalyzed Henry Reaction. Asymmetric Syntheses of (−)-Denopamine and (−)-Arbutamine

Barry M. Trost,* Vince S. C. Yeh, Hisanako Ito, and Nadine Bremeyer
Department of Chemistry, Stanford University, Stanford, California 94305-5080
Org. Lett., 2002, 4 (16), pp 2621–2623
DOI: 10.1021/ol020077n
Publication Date (Web): July 19, 2002
Copyright © 2002 American Chemical Society

Abstract

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Syntheses of variously modified ligands for the dinuclear zinc catalysts for the asymmetric aldol and nitroaldol (Henry) reactions are reported. Catalytic enantioselective nitroaldol reactions promoted by these modified ligands led to efficient syntheses of the β-receptor agonists (−)-denopamine and (−)-arbutamine.

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History

  • Published In Issue August 08, 2002
  • Received April 15, 2002

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