Reductive Removal of the Pivaloyl Protecting Group from Tetrazoles by a Naphthalene-Catalyzed Lithiation Process
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| Title: | Reductive Removal of the Pivaloyl Protecting Group from Tetrazoles by a Naphthalene-Catalyzed Lithiation Process |
|---|---|
| Authors: | Behloul, Cherif | Chouti, Aicha | Guijarro, David | Nájera, Carmen | Yus, Miguel |
| Research Group/s: | Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | Síntesis Asimétrica (SINTAS) |
| Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
| Keywords: | Tetrazoles | Pivaloyl | Lithium | Deprotection |
| Knowledge Area: | Química Orgánica |
| Issue Date: | 27-Nov-2014 |
| Publisher: | Georg Thieme Verlag |
| Citation: | Synthesis. 2015, 47(04): 507-510. doi:10.1055/s-0034-1378681 |
| Abstract: | The reaction of various 1-pivaloyl-1H-tetrazoles with excess lithium and a catalytic amount of naphthalene (20 mol%) led, after treatment with methanol, to the corresponding free tetrazoles through reductive C–N bond cleavage. This methodology represents a reasonable alternative to other nonreductive protocols. |
| Sponsor: | This work was financially supported by the A.N.D.R.S. (Agence Nationale pour le Développement de la Recherche en Santé) (Algérie) and the Department of Organic Chemistry of the University of Alicante (Spain). We are very grateful to the Spanish Ministerio de Asuntos Exteriores y de Cooperación for a cooperation grant (AP/039112/11). |
| URI: | http://hdl.handle.net/10045/48288 |
| ISSN: | 0039-7881 (Print) | 1437-210X (Online) |
| DOI: | 10.1055/s-0034-1378681 |
| Language: | eng |
| Type: | info:eu-repo/semantics/article |
| Rights: | © Georg Thieme Verlag Stuttgart · New York |
| Peer Review: | si |
| Publisher version: | http://dx.doi.org/10.1055/s-0034-1378681 |
| Appears in Collections: | INV - CESO - Artículos de Revistas INV - SINTAS - Artículos de Revistas |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
 2015_Behloul_etal_Synthesis_final.pdf | Versión final (acceso restringido) | 165,29 kB | Adobe PDF | Open Request a copy |
 2015_Behloul_etal_Synthesis_rev.pdf | Versión revisada (acceso abierto) | 89,26 kB | Adobe PDF | Open Preview |
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