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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Enantioselective Henry reaction catalyzed with copper(II)–iminopyridine complexes
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A highly anti-selective asymmetric Henry reaction catalyzed by a chiral copper complex: applications to the syntheses of (+)-spisulosine and a pyrroloisoquinoline derivative.
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Enantioselective Henry reaction catalyzed by optically active ketoiminatocobalt complexes
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Highly Enantioselective Henry Reactions in Water Catalyzed by a Copper Tertiary Amine Complex and Applied in the Synthesis of (S)-N-trans-Feruloyl Octopamine
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TL;DR: A highly enantioselective Lewis acid catalyzed nitroaldol reaction with water as the solvent and Excellent yields (99%) and ee values (99 %) were achieved for a wide range of aldehydes.
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Mechanistic Insights on Cooperative Catalysis through Computational Quantum Chemical Methods
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