Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
A primary amine-salicylamide derived from chiral trans-cyclohexane-1,2-diamine was used as an organocatalyst for the enantioselective conjugate addition of aldehydes, mainly ,-disubstituted to N-substituted maleimides. The reaction was performed in toluene as a solvent at room temperature. The corre...
| Autores: | , , , , , |
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| Formato: | artículo |
| Fecha de publicación: | 2018 |
| País: | España |
| Recursos: | Universidad del País Vasco |
| Repositorio: | Addi. Archivo Digital para la Docencia y la Investigación |
| OAI Identifier: | oai:addi.ehu.eus:10810/31826 |
| Acesso em linha: | http://hdl.handle.net/10810/31826 |
| Access Level: | acceso abierto |
| Palavra-chave: | organocatalysis asymmetric synthesis Michael addition maleimides aldehydes alpha alpha-disubstituted aldehydes conjugate addition gamma-lactams ab-initio inhibitors thermochemistry protease catalyst |
| Resumo: | A primary amine-salicylamide derived from chiral trans-cyclohexane-1,2-diamine was used as an organocatalyst for the enantioselective conjugate addition of aldehydes, mainly ,-disubstituted to N-substituted maleimides. The reaction was performed in toluene as a solvent at room temperature. The corresponding enantioenriched adducts were obtained with high yields and enantioselectivities up to 94%. Theoretical calculations were used to justify the stereoinduction. |
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