The Versatility of the Roskamp Homologation in Synthesis
Modern organic synthesis continues to benefit from the flexibility of α-diazo carbonyl intermediates. In the context of homologation processes, the Roskamp reaction—first introduced in 1989—has become a valuable tool due to its selectivity and mild condition reactions for accessing important synthon...
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MDPI AG
2025-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/6/1192 |
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| author | Margherita Miele Aljoša Smajić Vittorio Pace |
| author_facet | Margherita Miele Aljoša Smajić Vittorio Pace |
| author_sort | Margherita Miele |
| collection | DOAJ |
| description | Modern organic synthesis continues to benefit from the flexibility of α-diazo carbonyl intermediates. In the context of homologation processes, the Roskamp reaction—first introduced in 1989—has become a valuable tool due to its selectivity and mild condition reactions for accessing important synthons amenable to further functionalization as β-keto esters. The fine-tuning of reaction parameters—including the nature of Lewis acids, solvents, and temperature—has enabled the development of catalyzed continuous-flow methodologies, as well as a series of asymmetric variants characterized by high transformation rates, excellent stereocontrol, and formidable chemoselectivity. This review aims to emphasize the attractive features of the Roskamp reaction and its applicability for addressing challenging homologation processes. |
| format | Article |
| id | doaj-art-397a6b57be1f4439b2b105f609aa1615 |
| institution | DOAJ |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-397a6b57be1f4439b2b105f609aa16152025-08-20T02:42:22ZengMDPI AGMolecules1420-30492025-03-01306119210.3390/molecules30061192The Versatility of the Roskamp Homologation in SynthesisMargherita Miele0Aljoša Smajić1Vittorio Pace2Department of Chemistry, University of Turin, Via P. Giuria 7, 10125 Turin, ItalyDivision of Pharmaceutical Chemistry, Department of Pharmaceutical Sciences, University of Vienna, Josef-Holaubek-Platz 2, A-1090 Vienna, AustriaDepartment of Chemistry, University of Turin, Via P. Giuria 7, 10125 Turin, ItalyModern organic synthesis continues to benefit from the flexibility of α-diazo carbonyl intermediates. In the context of homologation processes, the Roskamp reaction—first introduced in 1989—has become a valuable tool due to its selectivity and mild condition reactions for accessing important synthons amenable to further functionalization as β-keto esters. The fine-tuning of reaction parameters—including the nature of Lewis acids, solvents, and temperature—has enabled the development of catalyzed continuous-flow methodologies, as well as a series of asymmetric variants characterized by high transformation rates, excellent stereocontrol, and formidable chemoselectivity. This review aims to emphasize the attractive features of the Roskamp reaction and its applicability for addressing challenging homologation processes.https://www.mdpi.com/1420-3049/30/6/1192homologationRoskamp reactionasymmetric reactionα-diazocarbonyl compoundsWeinreb amidesα-silyl ketones |
| spellingShingle | Margherita Miele Aljoša Smajić Vittorio Pace The Versatility of the Roskamp Homologation in Synthesis Molecules homologation Roskamp reaction asymmetric reaction α-diazocarbonyl compounds Weinreb amides α-silyl ketones |
| title | The Versatility of the Roskamp Homologation in Synthesis |
| title_full | The Versatility of the Roskamp Homologation in Synthesis |
| title_fullStr | The Versatility of the Roskamp Homologation in Synthesis |
| title_full_unstemmed | The Versatility of the Roskamp Homologation in Synthesis |
| title_short | The Versatility of the Roskamp Homologation in Synthesis |
| title_sort | versatility of the roskamp homologation in synthesis |
| topic | homologation Roskamp reaction asymmetric reaction α-diazocarbonyl compounds Weinreb amides α-silyl ketones |
| url | https://www.mdpi.com/1420-3049/30/6/1192 |
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