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
Synthesis and luminescence studies of mono- and C3-symmetric, tris(ligand) complexes of Sm(III), Y(III) and Eu(III) with sulfur-bridged binaphtholate ligands.
TL;DR: Emission spectroscopy is sought to use as a non-invasive technique to monitor a monomer-dimer equilibrium in these complexes of a sulfur-bridged binaphthol ligand to demonstrate the potential use of such a technique.
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Convenient Preparation of Lanthanide Aryloxides from Lanthanide Nitrate Polyether Complexes and the Crystal Structure of [La(OC6H3Me2-2,6)3(MeO(CH2CH2O)4Me)]
Helen C. Aspinall,Mark Williams +1 more
TL;DR: In this paper, the use of easily prepared lanthanide nitrate polyether complexes in the synthesis of 2,6-dimethylphenoxides was reported, and the crystal structure of 8-coordinate [La(OC6H3Me2-2,6)3(tetraglyme)
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Asymmetric Henry reaction catalyzed by Cu(II)-based chiral amino alcohol complexes with C2-symmetry
Gonghao Lu,Fei Zheng,Lei Wang,Yuxin Guo,Xue Li,Xianjun Cao,Cuiping Wang,Haijun Chi,Yan Dong,Zhiqiang Zhang +9 more
TL;DR: In this paper, a series of chiral amino alcohol ligands were used as catalysts in asymmetric Henry reactions in the presence of Cu(II) ions giving good yields (up to 97%) and enantiomeric excesses (i.e., up to 98%).
Journal ArticleDOI
Cyclen-catalyzed Henry reaction under neutral conditions
TL;DR: In this paper, a cyclen-catalyzed Henry reaction of aldehydes with nitroalkanes under mild and neutral conditions is reported, which constitutes the first cyclen catalyzed synthesis of nitroalcohols and is adapted to the condensation of both aromatic and aliphatic aldehs with nitromethane in THF at room temperature without addition of stoichiometric amount of the base.
Journal ArticleDOI
An efficient and stereoselective route to 1-deoxy-5-hydroxy sphingosine analogues
TL;DR: A short and efficient synthesis of 1-deoxy-5-hydroxy sphingolipid is described, using a Jacobsen hydrolytic kinetic resolution and Shibasaki’s asymmetric Henry reaction.
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