Journal ArticleDOI
Basic character of rare earth metal alkoxides. Utilization in catalytic C-C bond-forming reactions and catalytic asymmetric nitroaldol reactions
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In this article, the authors reported several carbon-carbon bond-forming reactions catalyzed by rare earth metal alkoxides and their application to a catalytic asymmetric nitroaldol reaction.Abstract:
In a recent paper, the authors reported that Zr(O-t-Bu){sub 4} was an efficient and convenient basic reagent in organic synthesis. However, all reactions examined were performed with stoichiometric quantities of the reagent. The authors envisioned that rare earth metal alkoxides would be stronger bases than group 4 metal alkoxides due to the lower ionization potential (ca. 5.4-6.4 eV) and the lower electronegativity (1.1-1.3) of rare earth elements; thus, the catalytic use of rare earth metal alkoxides in organic synthesis was expected. Although a variety of rare earth metal alkoxides have been prepared for the last three decades, to the authors knowledge, there have been few reports concerning the basicity of rare earth metal alkoxides. Herein, the authors report several carbon-carbon bond-forming reactions catalyzed by rare earth metal alkoxides and their application to a catalytic asymmetric nitroaldol reaction.read more
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Michael reaction of 1,3-dicarbonyls with enones catalyzed by a hydroxyapatite-bound La complex
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Synthesis of tetrahydroisoquinoline (TIQ)-oxazoline ligands and their application in enantioselective Henry reactions
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TL;DR: In this article, a family of eleven new tetrahydroisoquinoline (TIQ)-oxazoline intermediates and five corresponding copper(II) catalysts has been developed and applied to the catalytic asymmetric Henry reacti...
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Novel thiolated amino-alcohols as chiral ligands for copper-catalyzed asymmetric nitro-aldol reactions
Woraluk Mansawat,Ittiphol Saengswang,Palita U-prasitwong,Worawan Bhanthumnavin,Tirayut Vilaivan +4 more
TL;DR: In this paper, Thiolated amino-alcohols have been synthesized and evaluated as a potential new class of chiral ligands for copper-catalyzed nitro-aldol reactions.
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Asymmetric Henry reaction catalyzed by bifunctional copper-based catalysts.
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