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
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

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