Dr. Caterina Damiano, Matteo Cavalleri, Prof. Corrado di Natale', Prof. Roberto Paolesse, Prof. Emma Gallo
A new photoactive material was obtained by the heterogenization of zinc(II) porphyrin onto cellulose-based Colour Catcher® sheet. The so-obtained Zn(porphyrin)@CC material performed very well in activating molecular oxygen in the photooxidative coupling of amines to imines and the photooxidation of aldehydes to corresponding acids in the presence of white light. The high eco-compatibility of the solid support, the chemical stability of the photoactive material and the mild experimental conditions applied confer a very good sustainability to the procedure and open the doors to a larger employment of Colour Catcher®-based porphyrin material in reactions mediated by light.
{"title":"Porphyrins Anchored onto Colour Catcher®: Photoactive Material for the Conversion of Amines into Imines and Aldehydes into Carboxylic Acids","authors":"Dr. Caterina Damiano, Matteo Cavalleri, Prof. Corrado di Natale', Prof. Roberto Paolesse, Prof. Emma Gallo","doi":"10.1002/ceur.202300020","DOIUrl":"https://doi.org/10.1002/ceur.202300020","url":null,"abstract":"<p>A new photoactive material was obtained by the heterogenization of zinc(II) porphyrin onto cellulose-based Colour Catcher® sheet. The so-obtained Zn(porphyrin)@CC material performed very well in activating molecular oxygen in the photooxidative coupling of amines to imines and the photooxidation of aldehydes to corresponding acids in the presence of white light. The high eco-compatibility of the solid support, the chemical stability of the photoactive material and the mild experimental conditions applied confer a very good sustainability to the procedure and open the doors to a larger employment of Colour Catcher®-based porphyrin material in reactions mediated by light.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"1 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202300020","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"50122099","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Lotte Stockhammer, Rebecca Craik, Prof. Dr. Uwe Monkowius, Dr. David B. Cordes, Prof. Dr. Andrew D. Smith, Prof. Dr. Mario Waser
The enantioselective α-functionalisation of glycine Schiff base aryl esters through isothiourea catalysis is successfully demonstrated for 1,6-additions to para-quinone methides (21 examples, up to 95 : 5 dr and 96 : 4 er) and 1,4- additions to methylene substituted dicarbonyl or disulfonyl Michael acceptors (17 examples, up to 98 : 2 er). This nucleophilic organocatalysis approach gives access to a range of α-functionalised α-amino acid derivatives and further transformations of the activated aryl ester group provide a straightforward entry to advanced amino acid-based esters, amides or thioesters.
{"title":"Isothiourea-Catalyzed Enantioselective Functionalisation of Glycine Schiff Base Aryl Esters via 1,6- and 1,4-Additions","authors":"Lotte Stockhammer, Rebecca Craik, Prof. Dr. Uwe Monkowius, Dr. David B. Cordes, Prof. Dr. Andrew D. Smith, Prof. Dr. Mario Waser","doi":"10.1002/ceur.202300015","DOIUrl":"https://doi.org/10.1002/ceur.202300015","url":null,"abstract":"<p>The enantioselective α-functionalisation of glycine Schiff base aryl esters through isothiourea catalysis is successfully demonstrated for 1,6-additions to para-quinone methides (21 examples, up to 95 : 5 dr and 96 : 4 er) and 1,4- additions to methylene substituted dicarbonyl or disulfonyl Michael acceptors (17 examples, up to 98 : 2 er). This nucleophilic organocatalysis approach gives access to a range of α-functionalised α-amino acid derivatives and further transformations of the activated aryl ester group provide a straightforward entry to advanced amino acid-based esters, amides or thioesters.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"1 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202300015","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"50119571","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Jonas Feldmann, Mads K. Skaanning, Marcus Lommel, Tobias Kernmayr, Dr. Peter Mayer, Prof. Dr. Thomas Carell
The question of how nucleosides might have formed as essential precursor molecules on the early Earth is one of the many challenges associated with the origin of life. In this context, the prebiotic synthesis of pyrimidine nucleosides is controversially discussed. For the pyrimidines, two at first glance contradictory prebiotically plausible reaction pathways have been proposed, based on either oxazole or isoxazole chemistry. This study shows that these two reaction sequences can be merged under prebiotically reasonable conditions, suggesting that both pathways could have co-existed and possibly interacted. The key precursor 3-aminoisoxazole was found to react with the key intermediate of the oxazole route (ribo-2-(methylthio)oxazoline), to form a ribo-isoxazole-oxazoline hybrid structure, which collapses upon reductive N−O bond cleavage to give the nucleoside cytidine. The data suggest that different, interacting prebiotically plausible chemical pathways may have created the key molecules of life on the early Earth.
{"title":"A Unifying Concept for the Prebiotic Formation of RNA Pyrimidine Nucleosides","authors":"Jonas Feldmann, Mads K. Skaanning, Marcus Lommel, Tobias Kernmayr, Dr. Peter Mayer, Prof. Dr. Thomas Carell","doi":"10.1002/ceur.202300013","DOIUrl":"https://doi.org/10.1002/ceur.202300013","url":null,"abstract":"<p>The question of how nucleosides might have formed as essential precursor molecules on the early Earth is one of the many challenges associated with the origin of life. In this context, the prebiotic synthesis of pyrimidine nucleosides is controversially discussed. For the pyrimidines, two at first glance contradictory prebiotically plausible reaction pathways have been proposed, based on either oxazole or isoxazole chemistry. This study shows that these two reaction sequences can be merged under prebiotically reasonable conditions, suggesting that both pathways could have co-existed and possibly interacted. The key precursor 3-aminoisoxazole was found to react with the key intermediate of the oxazole route (ribo-2-(methylthio)oxazoline), to form a ribo-isoxazole-oxazoline hybrid structure, which collapses upon reductive N−O bond cleavage to give the nucleoside cytidine. The data suggest that different, interacting prebiotically plausible chemical pathways may have created the key molecules of life on the early Earth.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"1 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2023-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202300013","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"50155303","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Great Expectations","authors":"L. De Cola, Ken Tanaka, Ive Hermans","doi":"10.1002/ceur.202200001","DOIUrl":"https://doi.org/10.1002/ceur.202200001","url":null,"abstract":"","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"51 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2022-12-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86809817","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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