Enantioselective Annulation Reactions of Bisenolates Prepared Through Dearomatization Reactions of Aromatic and Heteroaromatic Diesters

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dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Molecularesgl
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánicagl
dc.contributor.authorPérez-Vázquez, Jaime
dc.contributor.authorVeiga, Alberte X.
dc.contributor.authorPrado, Gustavo
dc.contributor.authorSardina López, Francisco Javier
dc.contributor.authorPaleo Pillado, María Rita
dc.date.accessioned2018-07-06T13:49:10Z
dc.date.available2018-07-06T13:49:10Z
dc.date.issued2012
dc.descriptionThis is the peer reviewed version of the following article: Pérez-Vázquez, J., Veiga, A., Prado, G., Sardina, F., & Paleo, M. (2012). Enantioselective Annulation Reactions of Bisenolates Prepared Through Dearomatization Reactions of Aromatic and Heteroaromatic Diesters. European Journal Of Organic Chemistry, 2012(5), 975-987, which has been published in final form at https:// doi.org/10.1002/ejoc.201101427. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions
dc.description.abstractA one‐pot, enantioselective strategy for the dearomatization–annulation of aromatic diesters to give a range of highly functionalized polycyclic molecules with excellent enantioselectivity is presented. This methodology is based on the reaction of bisenolates, prepared by treating aromatic diesters with trialkyltin lithium reagents, which involves a stanna‐Brook rearrangement, with 1,ω‐dihaloalkanes and other biselectrophiles. We have also developed experimental conditions for performing these reactions with substoichiometric amounts of the required tin reagent by in situ recycling of Me6Sn2 into Me3SnLi with excess lithium metal, and provide a study of the scope and limitations of this synthetic methodologygl
dc.description.peerreviewedSIgl
dc.description.sponsorshipFinancial support from Spanish MCYT (fellowship to A. V.) and Xunta de Galicia (Grants 10PXIB209113PR and 10PXIB209155PR) is gratefully acknowledgedgl
dc.identifier.citationPérez-Vázquez, J., Veiga, A., Prado, G., Sardina, F., & Paleo, M. (2011). Enantioselective Annulation Reactions of Bisenolates Prepared Through Dearomatization Reactions of Aromatic and Heteroaromatic Diesters. European Journal Of Organic Chemistry, 2012(5), 975-987. doi: 10.1002/ejoc.201101427gl
dc.identifier.doi10.1002/ejoc.201101427
dc.identifier.essn1099-0690
dc.identifier.urihttp://hdl.handle.net/10347/16981
dc.language.isoenggl
dc.publisherWileygl
dc.relation.publisherversionhttps://doi.org/10.1002/ejoc.201101427gl
dc.rights© 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archivinggl
dc.rights.accessRightsopen accessgl
dc.subjectDearomatization-alkylationgl
dc.subjectStanna-Brookgl
dc.subjectBis-enolategl
dc.subjectAnnulationgl
dc.subjectEnantioselective alkylationgl
dc.titleEnantioselective Annulation Reactions of Bisenolates Prepared Through Dearomatization Reactions of Aromatic and Heteroaromatic Diestersgl
dc.typejournal articlegl
dc.type.hasVersionAMgl
dspace.entity.typePublication
relation.isAuthorOfPublicationd2ead1ad-132f-4d2d-9aff-5d8afd8237c9
relation.isAuthorOfPublicationff51de10-efdc-4fd3-9fab-8f2ab82f663b
relation.isAuthorOfPublication.latestForDiscoveryd2ead1ad-132f-4d2d-9aff-5d8afd8237c9

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