Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from N-tert-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds
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Título: | Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from N-tert-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds |
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Autor/es: | Sirvent, Ana | Foubelo, Francisco | Yus, Miguel |
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: | Chiral sulfinyl imines | Functionalized organolithium compounds | Diastereoselective additions | Piperidine alkaloids | Isosolenopsin A |
Área/s de conocimiento: | Química Orgánica |
Fecha de publicación: | 28-oct-2021 |
Editor: | MDPI |
Cita bibliográfica: | Sirvent A, Foubelo F, Yus M. Stereoselective Synthesis of δ- and ε-Amino Ketone Derivatives from N-tert-Butanesulfinyl Aldimines and Functionalized Organolithium Compounds. Molecules. 2021; 26(21):6503. https://doi.org/10.3390/molecules26216503 |
Resumen: | The addition of functionalized organolithium compounds derived from 5-chloro-2-methoxy-1-pentene and 6-chloro-2-methoxy-1-hexene to N-tert-butanesulfinyl aldimines imines, and a subsequent hydrolysis of the enol ether moiety, yielded different δ- and ε-amino ketone derivatives, respectively, in moderate yields and diastereoselectivities. The application of these compounds in organic synthesis was demonstrated by the preparation of 2-substituted 6-methylpiperidines in a stereoselective manner, among them natural alkaloids (+)- and (−)-isosolenopsin A. |
Patrocinador/es: | This research was supported by the Spanish Ministerio de Economía y Competitividad (MINECO; projects Funding: CTQ2014–53695-P, CTQ2014-51912-REDC, CTQ2016-81797-REDC, CTQ2017-85093-P), Ministerio de Ciencia, Innovación y Universidades (RED2018-102387-T, PID2019-107268GB-100), FEDER, the Generalitat Valenciana (PROMETEOII/2014/017), and the University of Alicante (VIGROB-068). |
URI: | http://hdl.handle.net/10045/119009 |
ISSN: | 1420-3049 |
DOI: | 10.3390/molecules26216503 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.3390/molecules26216503 |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas |
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