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EnglishThe synthesis of (2S,4R)- and (2R,4R)-4-hydroxypipecolic acid has been realized from commercial ethyl (R)-4-cyano-3-hydroxybutanoate through palladium-catalyzed methoxycarbonylation of a 4-hydroxy-substituted lactam-derived vinyl phosphate followed by the stereocontrolled reduction of the enamine double bond. The stereoselective hydrogenation of the suitably 4-hydroxy-protected enantiomer afforded the cis-(2S,4R)-4-hydroxypipecolic acid product, obtained in 66% overall yield over seven steps. The trans-product (42% overall yield over 8 steps) was instead obtained by hydride conjugate addition to the same α,β-unsaturated ester.
| Titolo: | A Short and Convenient Synthesis of Enantiopure cis- and trans-4-Hydroxypipecolic Acid |
| Autori Riconosciuti: | |
| Autori: | Ernesto G. Occhiato; Dina Scarpi; Antonio Guarna; Silvia Tabasso; Annamaria Deagostino; Cristina Prandi |
| Data di pubblicazione: | 2009 |
| Abstract: | The synthesis of (2S,4R)- and (2R,4R)-4-hydroxypipecolic acid has been realized from commercial ethyl (R)-4-cyano-3-hydroxybutanoate through palladium-catalyzed methoxycarbonylation of a 4-hydroxy-substituted lactam-derived vinyl phosphate followed by the stereocontrolled reduction of the enamine double bond. The stereoselective hydrogenation of the suitably 4-hydroxy-protected enantiomer afforded the cis-(2S,4R)-4-hydroxypipecolic acid product, obtained in 66% overall yield over seven steps. The trans-product (42% overall yield over 8 steps) was instead obtained by hydride conjugate addition to the same α,β-unsaturated ester. |
| Volume: | - |
| Pagina iniziale: | 3611 |
| Pagina finale: | 3616 |
| Digital Object Identifier (DOI): | 10.1055/s-0029-1216979 |
| URL: | https://www.thieme-connect.de/DOI/DOI?10.1055/s-0029-1216979 |
| Rivista: | SYNTHESIS |
| Appare nelle tipologie: | 03A-Articolo su Rivista |
File in questo prodotto:
| File | Descrizione | Tipologia | Licenza | |
|---|---|---|---|---|
| Synthesis.doc | POSTPRINT (VERSIONE FINALE DELL’AUTORE) | Accesso aperto | Open Access Visualizza/Apri | |
| synthesis2009.pdf | PDF EDITORIALE | Utenti riconosciuti Richiedi una copia |
http://hdl.handle.net/2318/132203
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