Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate
The comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Brønsted acid catalyst is described. In result, a broad range of 3-oxo-esters were synthesized from a variety of ketones and aliphatic aldehydes by 1,2-aryl/alkyl/hydride shift. Aryl–methyl ket...
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| Veröffentlicht in: | Journal of organic chemistry 2021-05, Vol.86 (9), p.6138-6147 |
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| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | The comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Brønsted acid catalyst is described. In result, a broad range of 3-oxo-esters were synthesized from a variety of ketones and aliphatic aldehydes by 1,2-aryl/alkyl/hydride shift. Aryl–methyl ketones produced only aryl-migrated products, whereas other ketones yielded a mixture of products. For diaryl ketones, the identity of two inseparable migrated products was confirmed by two-dimensional NMR spectroscopy. |
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| ISSN: | 0022-3263 1520-6904 |
| DOI: | 10.1021/acs.joc.0c02972 |