Diastereoselective multicomponent Amine-Aldehyde-Dienophile (AAD) process for the synthesis of polysubstituted cyclohex-2-enylamines
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| Title: | Diastereoselective multicomponent Amine-Aldehyde-Dienophile (AAD) process for the synthesis of polysubstituted cyclohex-2-enylamines |
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| Authors: | Selva, Verónica | Chabour, Ihssene | Nájera, Carmen | Sansano, Jose M. |
| Research Group/s: | Síntesis Asimétrica (SINTAS) |
| Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
| Keywords: | Multicomponent | AAD | Cyclohex-2-enylamine | Diels-Alder | Primary amines |
| Knowledge Area: | Química Orgánica |
| Issue Date: | 8-Mar-2019 |
| Publisher: | Elsevier |
| Citation: | Tetrahedron. 2019, 75(10): 1315-1321. doi:10.1016/j.tet.2019.01.063 |
| Abstract: | The multicomponent Amine-Aldehyde-Dienophile reaction is optimized employing benzyl or 4-methoxybenzylamine. The interest of the transformation consist in the synthesis of polysubstituted cyclohex-2-enylamines. The study of the scope of this AAD process is carried out, as well as the diastereoselective version, employing commercially available chiral benzylic amines and a maleimide with the chiral information at the N-substituent. VCD spectroscopy is a very useful tool for the determination of the absolute configuration of the isolated enantiomerically enriched compounds. |
| Sponsor: | We gratefully acknowledge financial support from the Spanish Ministerio de Economía y Competitividad (MINECO), Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (Project Nos. CTQ2013-43446-P, CTQ2014-51912-REDC, CTQ2016-76782-P, CTQ2016-81797-REDC, CTQ2016-81893REDT, and CTQ2016-76155-R), the Generalitat Valenciana (PROMETEOII/2014/017) and the University of Alicante. |
| URI: | http://hdl.handle.net/10045/88292 |
| ISSN: | 0040-4020 (Print) | 1464-5416 (Online) |
| DOI: | 10.1016/j.tet.2019.01.063 |
| Language: | eng |
| Type: | info:eu-repo/semantics/article |
| Rights: | © 2019 Elsevier Ltd. |
| Peer Review: | si |
| Publisher version: | https://doi.org/10.1016/j.tet.2019.01.063 |
| Appears in Collections: | INV - SINTAS - Artículos de Revistas |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
 2019_Veronica-Selva_etal_Tetrahedron_final.pdf | Versión final (acceso restringido) | 753,64 kB | Adobe PDF | Open Request a copy |
 2019_Veronica-Selva_etal_Tetrahedron_accepted.pdf | Accepted Manuscript (acceso abierto) | 672,75 kB | Adobe PDF | Open Preview |
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