[reaction: see text] Enantioselective borohydride reduction, catalyzed by the optically active beta-ketoiminato cobalt(II) complex, was successfully applied to the 1,1'-dialkanoyl- and 1,1'-dibenzoylferrocenes to afford the corresponding C(2)-symmetrical chiral ferrocenyl diols with high diastereoselectivity and excellent enantioselectivity.
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Org Lett
October 2024
Department of Chemistry, Graduate School of Science and Soft Molecular Activation Research Center, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
An oxidative remote aryl rearrangement of -cinnamyl--alkoxybenzyl sulfonamides with a hypervalent iodine(III) compound was developed to furnish 5,6-disubstituted 1,3-oxazinanes in high yields. This reaction proceeded through the dearomatization of the alkoxybenzene ring on the benzyl group, which acts as a good aryl donor, inducing the regioselective installation of the aryl group and the oxygen atom via cascade transformation. An enantioselective oxidative remote aryl rearrangement using C2-symmetrical chiral iodoarene gave enantioenriched products with high enantioselectivity.
View Article and Find Full Text PDFChemistry
January 2024
State Key Lab of Metal Matrix Composites, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Materials Science and Engineering, Shanghai Jiaotong University, Dongchuan Rd 800, 200240, Shanghai, China.
To comprehend the significance of improved conductive properties in C2-symmetric hydrogels, it is vital to investigate how non-gelating achiral functional group isomers influence the conductivity of such supramolecular hydrogels, whereas understanding the major driving forces behind this regulatory process is first and foremost. Herein, we report a hydrogel system containing tryptophan-conjugated NDI as the backbone (L/D-NTrp), enabling effective supramolecular assembly with the bipyridyl functional group isomers. This co-assembly behavior results in materials with exceptional mechanical properties and high conductivities, surpassing most previously reported C2-symmetrical hydrogels, as well as the ability to form controlled morphologies.
View Article and Find Full Text PDFJ Org Chem
September 2022
Department of Chemistry and Industrial Chemistry, University of Pisa, via Moruzzi 13, 56124 Pisa, Italy.
A C2-symmetrical bis-thiourea chiral solvating agent (CSA), , for NMR spectroscopy has been obtained by reacting (1,2)-1,2-bis(2-hydroxyphenyl)ethylenediamine and 3,5-bis(trifluoromethyl)phenyl isothiocyanate. shows remarkable propensity to enantiodiscriminate -trifluoroacetyl (-TFA) and -acetyl (-Ac) derivatives of amino acids with free carboxyl functions, with the co-presence of 1,4-diazabicyclo[2.2.
View Article and Find Full Text PDFDalton Trans
September 2018
School of Chemistry, Trinity Biomedical Sciences Institute (TBSI), Trinity College Dublin, Dublin 2, Ireland.
Chiral lanthanide-based supramolecular structures have gained significant importance in view of their application in imaging, sensing and other functional purposes. We have designed chiral C2-symmetrical ligands (L) based on the use of two 2,6-pyridine-dicarboxylic-amide moieties (pda), that differ from one another by the nature of the diamine spacer groups (from 1,3-phenylenedimethanamine (1(S,S), 2(R,R)) and benzene-1,3-diamine (3(S,S), 4(R,R)) to much bulkier 4,4'-(cyclohexane-1,1-diyl)bis(2,6-dimethylaniline) (5(S,S), 6(R,R))) between these two pda units. The self-assembly between L and Eu(iii) ions were investigated in CH3CN solution at low concentration whereby the changes in the absorbance, fluorescence and Eu(iii)-centred emission spectra allowed us to model the binding equilibria occurring in the solution to the presence of [Eu:L2], [Eu2:L2], [Eu2:L3] assemblies and reveal their high binding constant values.
View Article and Find Full Text PDFChemistry
September 2016
Department of Chemistry, University of Milan, Via C. Golgi 19, 20133, Milan, Italy.
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