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The straightforward synthesis of polystyrene-supported Chinchona alkaloids and their application in the asymmetric dimerization of ketenes is reported. Six different immobilized derivatives, consisting of three dimeric and two monomeric 9-O ethers, were prepared by "click" anchoring of soluble alkaloid precursors on to azidomethyl resins. The resulting insoluble polymer-bound (IPB) organocatalysts were employed for promoting the dimerization of in-situ generated ketenes. After opening of the ketene dimer intermediates with N,O-dimethylhydroxylamine, valuable Weinreb amides were eventually obtained in good yield (up to 81%) and excellent enantiomeric purity (up to 96% ee). All of the IPB catalysts could be recycled effectively without significant loss of activity and enantioselectivity. The extension to other asymmetric transformations (meso-anhydride desymmetrization and α-amination of 2-oxindoles) is also briefly discussed. [ABSTRACT FROM AUTHOR]

Fish meal (FM) is an industrial product, mainly obtained from whole wild-caught fish, that is used as a high protein feedstuff component in aquaculture and intensive animal farming. Contamination of FM by microplastics (MPs), the synthetic polymer particles known to be nearly ubiquitous in the marine environment, is a likely consequence of their ingestion by zooplankton and other small marine animals that through the food chain end up in the fish commercialized not only for direct human consumption but also for the industrial production of FM. Unfortunately, analytical tools for quantifying contamination of FM by synthetic polymers are not available. A newly developed procedure described here allows quantification of the total amounts of polyolefins (including ethene and propene homo- and copolymers), polystyrene (PS), and poly(ethylene terephthalate) (PET), respectively, in FM. The multi-step procedure involves a sequence of solvent extractions, hydrolytic treatments to remove the biogenic matrix mainly consisting of proteins and some lipids, and selective depolymerization for PET. The gravimetric and SEC-UV techniques employed for the quantification of polyolefins and PS, respectively, only allowed to estimate their concentration in FM at around or below 100 mg/kg each, a more accurate quantification being prevented by the interference from the organic matrix and, in the case of polyolefins, by the limited sensitivity of the quantification by gravimetry. On the other hand, the contamination by PET MPs could accurately be quantified at 12.9 mg/kg based on the dry FM mass. Ways to overcome the sensitivity limitations for PS and polyolefins by using e.g. pyrolysis-GC/MS are highlighted., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2020 Elsevier Ltd. All rights reserved.)

The straightforward synthesis of polystyrene-supported Chinchona alkaloids and their application in the asymmetric dimerization of ketenes is reported. Six different immobilized derivatives, consisting of three dimeric and two monomeric 9-O ethers, were prepared by "click" anchoring of soluble alkaloid precursors on to azidomethyl resins. The resulting insoluble polymer-bound (IPB) organocatalysts were employed for promoting the dimerization of in-situ generated ketenes. After opening of the ketene dimer intermediates with N,O-dimethylhydroxylamine, valuable Weinreb amides were eventually obtained in good yield (up to 81 %) and excellent enantiomeric purity (up to 96 % ee). All of the IPB catalysts could be recycled effectively without significant loss of activity and enantioselectivity. The extension to other asymmetric transformations (meso-anhydride desymmetrization and α-amination of 2-oxindoles) is also briefly discussed., (© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)