We synthesized new organomanganese complexes using the phenolic "pincer" type ligand H-POP. The coordination chemistry of H-POP with Mn(i) was explored, revealing a wide range of binding motifs. Finally, we found that complex 1 catalyzes the formation of benzyl benzoate from benzaldehyde in a Tishchenko reaction.
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http://dx.doi.org/10.1039/c8dt02933d | DOI Listing |
J Org Chem
December 2024
Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973, Japan.
In this study, we analyzed the asymmetric aldol-Tishchenko reaction of α-fluoroarylketones with aldehydes in the presence of chiral lithium binaphtholate, which was readily prepared from a chiral BINOL derivative and lithium -butoxide. This tandem reaction afforded enantiomerically enriched 2-fluoro-1,3-diols with three contiguous stereogenic centers in high yield and with high diastereo- and enantioselectivities. Moreover, mechanistic investigations of the lithium binaphtholate-catalyzed enantioselective aldol-Tishchenko reaction were performed based on the kinetic isotope effect and computational analyses.
View Article and Find Full Text PDFInt J Mol Sci
October 2024
Department of Biochemistry and Cell Physiology, Voronezh State University, 394018 Voronezh, Russia.
Representatives of the colorless sulfur bacteria of the genus use reduced sulfur compounds in the processes of lithotrophic growth, which is accompanied by the storage of intracellular sulfur. However, it is still unknown how the transformation of intracellular sulfur occurs in representatives. Annotation of the genome of D-402 did not identify any genes for the oxidation or reduction of elemental sulfur.
View Article and Find Full Text PDFRSC Adv
May 2024
Advanced Catalysis Facility, Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology Vellore-632014 Tamil Nadu India
For over a century, the Tishchenko reaction has been a valuable technique for synthesizing esters from aldehydes, serving a variety of applications in different domains. Beyond the remarkable advances in organoactinide and organolanthanide chemistry over the past two decades, there has been a significant increase in the research of the electrophilic d0/fn chemistry of organoactinide and organolanthanide compounds due to the captivating interplay between their structure and reactivity, and their exceptional performance in various homogeneous catalytic processes. The remarkable influence of ligand design, both in terms of steric hindrance and electronic properties, on the catalytic activity of organo-f-element complexes in organic transformations is well-established.
View Article and Find Full Text PDFACS Omega
April 2024
Sanken, Osaka University, 8-1 Mihogaoka, Ibaraki 567-0047, Osaka, Japan.
A practical synthesis of -1,4-dialdehydes based on the oxidative cleavage of cyclobutanediol derivatives using polymer-supported periodate was developed. The -1,4-dialdehydes were obtained in up to >99% yield and subsequently employed in Ir-catalyzed asymmetric Tishchenko reactions to give the corresponding chiral lactones, which are versatile synthetic intermediates, in good yield with moderate enantiomeric excess. The catalytically active species was identified by means of cold-spray ionization mass spectrometry and H NMR spectroscopy.
View Article and Find Full Text PDFBeilstein J Org Chem
April 2023
Laboratoire de Synthèse Organique, Ecole Polytechnique, CNRS, ENSTA, Institut Polytechnique de Paris, 91128 Palaiseau, France.
Latrunculins are marine toxins used in cell biology to block actin polymerization. The development of new synthetic strategies and methods for their synthesis is thus important in order to improve, modulate or control this biological value. The total syntheses found in the literature all target similar disconnections, especially an aldol strategy involving a recurrent 4-acetyl-1,3-thiazolidin-2-one ketone partner.
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