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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Journal ArticleDOI
Asymmetric nitroaldol reaction with a chiral copper complex derived from D-tartaric acid
TL;DR: In this article, a tetradentate copper complex derived from D-tartaric acid was used to give β-nitroalkanols in moderate to high enantioselectivitie.
Journal ArticleDOI
Synthesis and structural characterization of a novel dinuclear Cu(II) complex: an efficient and recyclable bifunctional heterogeneous catalyst for the diastereoselective Henry reaction
Datta Markad,Sanjay K. Mandal +1 more
TL;DR: A novel dinuclear Cu(ii) complex containing a new flexible mixed pyridine-carboxylate ligand has been found to be an efficient, robust and recyclable heterogeneous catalyst for the diastereoselective Henry (nitroaldol) reaction of aldehydes with nitroethane.
Journal ArticleDOI
Catalytic asymmetric nitroaldol (Henry) reactions with copper(II)/cyclopropane-based bisoxazoline complexes
TL;DR: In this paper, cyclopropane-based bisoxazolines were synthesized from (R )- and (S )-amino alcohols, and applied to copper-catalyzed enantioselective nitroaldol reactions between nitromethane and various aldehydes.
Journal ArticleDOI
Asymmetric Enamide–Imine Tautomerism in the Kinetic Resolution of Tertiary Alcohols
TL;DR: In this paper, an asymmetric enamide-imine tautomerism process enabled by chiral phosphoric acid catalysis was developed for the resolution of tertiary alcohols.
Journal ArticleDOI
Uranium(IV) BINOLate Heterobimetallics: Synthesis and Reactivity in an Asymmetric Diels–Alder Reaction
TL;DR: In this article, the first heterobimetallic BINOLate complexes incorporating uranium were prepared, and their reactivity in an asymmetric Diels-Alder reaction was investigated; the contributions of both the Li+ and UIV cations to the reaction selectivity were addressed through control of the two different Lewis acidic centers.
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