Application of 1,3-Dipolar Reactions between Azomethine Ylides and Alkenes to the Synthesis of Catalysts and Biologically Active Compounds
The (3+2) cycloaddition between azomethine ylides and alkenes is an efficient, convergent and stereocontrolled method for the synthesis of unnatural pyrrolidine and proline scaffolds. In this review, the application of this reaction to the synthesis of enantiopure organometallic ligands for asymmetr...
| 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:10810/49812 |
| Acesso em linha: | http://hdl.handle.net/10810/49812 |
| Access Level: | acceso abierto |
| Palavra-chave: | 1,3-dipolar reactions cycloadditio asymmetric catalysis organocatalysis medicinal chemistry enantioselective synthesis 3+2 cycloaddition planar chirality proline esters p,n-ferrocene ligands conjugate addition ferrocenyl ligands allylic alkylation inhibitors stepwise |
| Resumo: | The (3+2) cycloaddition between azomethine ylides and alkenes is an efficient, convergent and stereocontrolled method for the synthesis of unnatural pyrrolidine and proline scaffolds. In this review, the application of this reaction to the synthesis of enantiopure organometallic ligands for asymmetric catalysis is presented first. These new EhuPhos ligands can participate in a second generation of 1,3-dipolar reactions that generate an offspring of unnatural proline derivatives that behave as efficient organocatalysts. These densely substituted unnatural l-proline derivatives exhibit distinct features, different to those described for natural l-proline and its derivatives. Finally, several examples of biologically active proline derivatives obtained by means of (3+2) cycloadditions involving azomethine ylides are presented. These applications show the character of privileged structures of these polysubstituted pyrrolidine rings. |
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