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
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.
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
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Appears in Collections:INV - SINTAS - Artículos de Revistas

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