Effect of Ligand Structure on the Zinc-Catalyzed Henry Reaction. Asymmetric Syntheses of (−)-Denopamine and (−)-Arbutamine
- 19 July 2002
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (16) , 2621-2623
- https://doi.org/10.1021/ol020077n
Abstract
[reaction: see text] 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 beta-receptor agonists (-)-denopamine and (-)-arbutamine.Keywords
This publication has 19 references indexed in Scilit:
- A Dinuclear Zn Catalyst for the Asymmetric Nitroaldol (Henry) Reaction We thank the National Science Foundation and the National Institutes of Health, General Medical Sciences, for their generous support of our programs. Mass spectra were provided by the Mass Spectrometry Facility of the University of California, San Francisco, supported by the NIH Division of Research Resources.Angewandte Chemie International Edition in English, 2002
- Direct Asymmetric Aldol Reactions of Acetone Using Bimetallic Zinc CatalystsOrganic Letters, 2001
- Asymmetric Aldol Reaction via a Dinuclear Zinc Catalyst: α-Hydroxyketones as DonorsJournal of the American Chemical Society, 2001
- A Direct Catalytic Enantioselective Aldol Reaction via a Novel Catalyst DesignJournal of the American Chemical Society, 2000
- Alkyl− and Aryl−Oxygen Bond Activation in Solution by Rhodium(I), Palladium(II), and Nickel(II). Transition-Metal-Based SelectivityJournal of the American Chemical Society, 1998
- Synthesis of macrocyclic polyhydroxy tetralactams derived from L-tartaric acid and β-hydroxyglutaric acidTetrahedron, 1997
- Asymmetric Catalysis with Heterobimetallic CompoundsAngewandte Chemie International Edition in English, 1997
- Efficient Diastereoselective and Enantioselective Nitroaldol Reactions from Prochiral Starting Materials: Utilization of La-Li-6,6'-Disubstituted BINOL Complexes as Asymmetric CatalystsThe Journal of Organic Chemistry, 1995
- Basic character of rare earth metal alkoxides. Utilization in catalytic carbon-carbon bond-forming reactions and catalytic asymmetric nitroaldol reactionsJournal of the American Chemical Society, 1992
- Formaldehyde condensations with phenol and its homologues. XII. The dehalogenation of halogenated diphenylmethanes having halogen substituents in the nucleusJournal of Chemical Technology & Biotechnology, 1951