Synthesis of perhydrofuro[2,3-b]furans from isopentenyl alcohol through carbonyl-ene and wacker-type reactions

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Title: Synthesis of perhydrofuro[2,3-b]furans from isopentenyl alcohol through carbonyl-ene and wacker-type reactions
Authors: Alonso, Francisco | Rodríguez Fernández, María del Carmen | Sánchez Terrés, Daniel | Yus, Miguel
Research Group/s: Nuevas Metodologías en Síntesis Orgánica
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica
Keywords: Natural products | Synthetic meth­ods | Oxygen heterocycles | Ene reaction | Wacker reaction | Perhydrofurofurans
Knowledge Area: Química Orgánica
Date Created: 2011
Issue Date: Nov-2011
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: ALONSO VALDÉS, Francisco, et al. "Synthesis of perhydrofuro[2,3-b]furans from isopentenyl alcohol through carbonyl-ene and wacker-type reactions". European Journal of Organic Chemistry. Vol. 2011, Issue 32 (Nov. 2011). ISSN 1434-193X, pp. 6459-6469
Abstract: A range of 2-substituted perhydrofuro[2,3-b]furans have been synthesized in a stereoselective manner through a sequence involving the Lewis-acid catalyzed carbonyl-ene reaction of a protected isopentenyl alcohol with a variety of enophiles, deprotection of the corresponding monoprotected diols, and palladium-catalyzed intramolecular acetalization under Wacker-type reaction conditions.
Sponsor: This work was generously supported by the Spanish Ministerio de Ciencia e Innovación (MICINN), grant number CTQ2007-65218 and Consolider Ingenio 2010, grant number CSD2007-00006, the Generalitat Valenciana (GV; PROMETEO/2009/039), and Fondos Europeos para el Desarrollo Regional (FEDER). D. S. thanks the Vicerrectorado de Investigación, Desarrollo e Innovación of the Universidad de Alicante for a predoctoral grant. M. R.-F. thanks the ISO of the Universidad de Alicante for a postdoctoral grant.
URI: http://hdl.handle.net/10045/19562
ISSN: 1434-193X (Print) | 1099-0690 (Online)
DOI: 10.1002/ejoc.201100961
Language: eng
Type: info:eu-repo/semantics/article
Rights: The definitive version is available at www3.interscience.wiley.com
Peer Review: si
Publisher version: http://dx.doi.org/10.1002/ejoc.201100961
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