“Side‐Product Catalysis”: Substrate Autoxidation as an Overlooked Side Reaction Generating a Co‐Catalyst for Enhancing Asymmetric Aldol Reactions

Heidlindemann, Marcel; Berkessel, Albrecht; Gröger, Harald

doi:10.1002/cctc.201601530

Cited by 6 publications

(1 citation statement)

References 89 publications

(79 reference statements)

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“…The following supporting information can be downloaded at https: //www.mdpi.com/article/10.3390/catal12040433/s1, Figure S1 S1: DLS analysis of 13a and SC5II with or without coordinated copper; Table S2: Elemental analysis of strains 13a and SC5II with or without Cu(II) or Cu(I) coordinated. References [18,38,44,45] are cited in the Supplementary Materials. Funding: The research and APC were supported by Fondazione CARIPLO-Circular Economy 2020 project num.…”

Section: Supplementary Materialsmentioning

confidence: 99%

Hybrid Catalysts from Copper Biosorbing Bacterial Strains and Their Recycling for Catalytic Application in the Asymmetric Addition Reaction of B2(pin)2 on α,β-Unsaturated Chalcones

et al. 2022

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The recycling of heavy metal contaminants from wastewater as a source of valuable products perfectly fits with the principles of a Circular Economy system in view of restoring pollutants back into the system endowed with new social and economic benefits. Heavy metals are often present in such a low concentration that it makes the removal efficiency difficult to realize through the conventional physicochemical methods with high selectivity. Biosorption, conversely, by EPSs (extracellular polymeric substances) produced by several bacterial cells’ strains, is gaining a great deal of attention as an economic, efficient and sustainable depolluting process of wastewater from metal cations such as copper. Metal coordination to EPS components was thus deeply investigated by 1H NMR titration experiments. The 1,10–Phenanthroline–copper complex was exploited for quantifying the ability of different strains to sequester copper by a practical UV-Vis spectrophotometric method. The obtained data distinguished Serratia plymuthica strain SC5II as the bacterial strain displaying copper-adsorbing properties higher than any other, with Stenotrophomonas sp. strain 13a resulting in the worst one. Different analytical techniques, i.e., Dynamic Light Scattering (DLS), FT-IR analysis and SEM spectroscopy were thus employed to rationalize these results. Finally, the obtained copper chelates were successfully employed as hybrid catalysts in the asymmetric boron addition to α,β-unsaturated chalcones for the synthesis of valuable pharmaceutical intermediates, thus placing waste management in a new circular perspective.

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Section: Supplementary Materialsmentioning

confidence: 99%

Hybrid Catalysts from Copper Biosorbing Bacterial Strains and Their Recycling for Catalytic Application in the Asymmetric Addition Reaction of B2(pin)2 on α,β-Unsaturated Chalcones

et al. 2022

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Cascade Reaction by Chemo‐ and Biocatalytic Approaches to Obtain Chiral Hydroxy Ketones and anti 1,3‐Diols

et al. 2018

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A chemo‐ and biocatalytic cascade approach was applied for the stereoselective synthesis of hydroxy ketones and the corresponding 1,3‐diols. A new class of tridentate N,N,O ligands was used with copper(II) complexes for the asymmetric β‐borylation of α,β‐unsaturated compounds. The complex containing ligand L5 emerged as the best performer, and it gave the organoborane derivatives with good ee values. The corresponding keto–alcohol compounds were then bioreduced by yeasts. The biotransformation set up with Rhodotorula rubra allowed (R)‐keto–alcohols and (S,S)‐diols to be obtained with up to 99 % ee and up to 99 % de in favor of the anti enantiomers.

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Screening of functional solvent system for automatic aldehyde and ketone separation in aldol reaction: A combined COSMO-RS and experimental approach

Zhang

Song

Jin

et al. 2020

Chemical Engineering Journal

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“Side‐Product Catalysis”: Substrate Autoxidation as an Overlooked Side Reaction Generating a Co‐Catalyst for Enhancing Asymmetric Aldol Reactions

Cited by 6 publications

References 89 publications

Hybrid Catalysts from Copper Biosorbing Bacterial Strains and Their Recycling for Catalytic Application in the Asymmetric Addition Reaction of B2(pin)2 on α,β-Unsaturated Chalcones

Hybrid Catalysts from Copper Biosorbing Bacterial Strains and Their Recycling for Catalytic Application in the Asymmetric Addition Reaction of B2(pin)2 on α,β-Unsaturated Chalcones

Cascade Reaction by Chemo‐ and Biocatalytic Approaches to Obtain Chiral Hydroxy Ketones and anti 1,3‐Diols

Screening of functional solvent system for automatic aldehyde and ketone separation in aldol reaction: A combined COSMO-RS and experimental approach

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