Stereoselective Synthesis of Densely Substituted Pyrrolidines via a [3 + 2] Cycloaddition Reaction between Chiral N-tert-Butanesulfinylazadienes and Azomethine Ylides
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Título: | Stereoselective Synthesis of Densely Substituted Pyrrolidines via a [3 + 2] Cycloaddition Reaction between Chiral N-tert-Butanesulfinylazadienes and Azomethine Ylides |
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Autor/es: | Blanco-López, Ester | Foubelo, Francisco | Retamosa, Maria de Gracia | Sansano, Jose M. |
Grupo/s de investigación o GITE: | Síntesis Asimétrica (SINTAS) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | N-tert-butanesulfinylimine | Azomethine ylides | Diastereoselective synthesis | Densely substituted pyrrolidines | 1,3-dipolar cycloadditions |
Fecha de publicación: | 4-oct-2023 |
Editor: | American Chemical Society |
Cita bibliográfica: | Organic Letters. 2023, 25(45): 8051-8056. https://doi.org/10.1021/acs.orglett.3c02572 |
Resumen: | The N-tert-butanesulfinylimine group behaves as a suitable electron-withdrawing group in 1-azadienes, allowing the diastereoselective synthesis of densely substituted pyrrolidines by 1,3-dipolar cycloadditions (1,3-DCs) with azomethylene ylides. The use of Ag2CO3 as catalyst has allowed one to obtain a wide variety of proline derivatives with high regio- and diastereoselectivities. Subsequent efficient transformations provide valuable proline derivatives, some of which can be used as organocatalysts. The influence of the N-tert-butanesulfinyl group on the diastereoselectivity was studied by computational methods. |
Patrocinador/es: | We gratefully acknowledge financial support from the Spanish Ministerio de Ciencia, Innovación y Universidades (project RED2018-102387-T), the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2017-82935-P and PID2019-107268GB-I00), the Generalitat Valenciana (IDIFEDER/2021/013, GVA-COVID19/2021/079, CIDEGENT/2020/058, CIAPOT/2022/11, and APOTIP/2021/020), Medalchemy S. L. (Medalchemy-18T), and the University of Alicante (VIGROB-068, UAUSTI21-05). |
URI: | http://hdl.handle.net/10045/137765 |
ISSN: | 1523-7060 (Print) | 1523-7052 (Online) |
DOI: | 10.1021/acs.orglett.3c02572 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 2022 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0. |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.1021/acs.orglett.3c02572 |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas |
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Archivo | Descripción | Tamaño | Formato | |
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Blanco-Lopez_etal_2023_OrgLett.pdf | 1,9 MB | Adobe PDF | Abrir Vista previa | |
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