Multicomponent synthesis of unnatural pyrrolizidines using 1,3-dipolar cycloaddition of proline esters
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Title: | Multicomponent synthesis of unnatural pyrrolizidines using 1,3-dipolar cycloaddition of proline esters |
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Authors: | Mancebo Aracil, Juan | Nájera, Carmen | Sansano, Jose M. |
Research Group/s: | Síntesis Asimétrica (SINTAS) |
Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica |
Keywords: | Pyrrolizidines | Synthesis | 1,3-dipolar cycloaddition | Proline esters |
Knowledge Area: | Química orgánica |
Issue Date: | 9-Oct-2013 |
Publisher: | Royal Society of Chemistry |
Citation: | Chem. Commun., 2013, 49, 11218-11220. doi:10.1039/c3cc47184e |
Abstract: | The synthesis of unnatural pyrrolizidines has been studied using a multicomponent-domino process involving proline or 4-hydroxyproline esters, an aldehyde and a dipolarophile. The formation of the iminium salt promotes the 1,3-dipolar cycloaddition affording highly substituted pyrrolizidines under mild conditions and high regio- and diastereoselectivities. |
Sponsor: | This work has been supported by the DGES of the Spanish Ministerio de Ciencia e Innovación (MICINN) (Consolider INGENIO 2010 CSD2007-00006, CTQ2007-62771/BQU, CTQ2010-20387), FEDER Generalitat Valenciana (PROMETEO/2009/039), and by the University of Alicante. |
URI: | http://hdl.handle.net/10045/33723 |
ISSN: | 1359-7345 (Print) | 1364-548X (Online) |
DOI: | 10.1039/c3cc47184e |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | © Royal Society of Chemistry 2013 |
Peer Review: | si |
Publisher version: | http://dx.doi.org/10.1039/c3cc47184e |
Appears in Collections: | INV - SINTAS - Artículos de Revistas |
Files in This Item:
File | Description | Size | Format | |
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chemcommunfinal.pdf | Article | 1 MB | Adobe PDF | Open Preview |
c3cc47184e.pdf | Supplementary information | 4,66 MB | Adobe PDF | Open Preview |
c3cc47184e.txt | Crystal structure data | 34,53 kB | Text | Open |
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