- -

Catalytic Asymmetric Formal [3+2] Cycloaddition of 2-Isocyanatomalonate Esters and Unsaturated Imines: Synthesis of Highly Substituted Chiral g-Lactams

RiuNet: Institutional repository of the Polithecnic University of Valencia

Share/Send to

Cited by

Statistics

Catalytic Asymmetric Formal [3+2] Cycloaddition of 2-Isocyanatomalonate Esters and Unsaturated Imines: Synthesis of Highly Substituted Chiral g-Lactams

Show simple item record

Files in this item

dc.contributor.author Espinosa, Miguel es_ES
dc.contributor.author Blay, Gonzalo es_ES
dc.contributor.author Cardona, Luz es_ES
dc.contributor.author Muñoz Roca, María Del Carmen es_ES
dc.contributor.author Pedro, José R. es_ES
dc.date.accessioned 2020-10-27T04:32:26Z
dc.date.available 2020-10-27T04:32:26Z
dc.date.issued 2017-10-20 es_ES
dc.identifier.issn 0947-6539 es_ES
dc.identifier.uri http://hdl.handle.net/10251/153234
dc.description.abstract [EN] Unlike their isocyano and isothiocyanato analogues, isocyanato esters remain almost unexplored as formal 1,3-dipoles in asymmetric catalytic reactions. The first asymmetric formal [3+2] cycloaddition involving isocyanato esters and electrophilic alkenes is reported. Diisopropyl 2-isocyanatomalonate reacts with a,b-unsaturated N-(o-anisidyl) imines in the presence of a Mg(OTf)2¿BOX complex to give highly substituted chiral pyrrolidinones featuring a conjugate exocyclic double bond with excellent yields and enantiomeric excesses up to 99%. Several transformations of the resulting heterocycles, including the synthesis of a pyroglutamic acid derivative, have been carried out. es_ES
dc.description.sponsorship Financial support (CTQ2013-47494-P) from the Ministerio de Economia y Competitividad (MINECO-Gobierno de Espana) is gratefully acknowledged. M.E. thanks the Generalitat Valenciana for a predoctoral grant. Access to the NMR and MS facilities from the Servei Central de Suport a la Investigacio Experimental (SCSIE)-UV is also acknowledged es_ES
dc.language Inglés es_ES
dc.publisher John Wiley & Sons es_ES
dc.relation info:eu-repo/grantAgreement/MINECO//CTQ2013-47494-P/ES/NUEVOS RETOS EN EL DESARROLLO DE PROCESOS ENANTIOSELECTIVOS DE FORMACION DE ENLACES C-C MEDIANTE CATALISIS DUAL COOPERATIVA./ es_ES
dc.relation.ispartof Chemistry - A European Journal es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Asymmetric catalysis es_ES
dc.subject Enantioselectivity es_ES
dc.subject Lactams es_ES
dc.subject Nitrogen heterocycles es_ES
dc.subject Nucleophilic addition es_ES
dc.subject.classification FISICA APLICADA es_ES
dc.title Catalytic Asymmetric Formal [3+2] Cycloaddition of 2-Isocyanatomalonate Esters and Unsaturated Imines: Synthesis of Highly Substituted Chiral g-Lactams es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1002/chem.201702777 es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Física Aplicada - Departament de Física Aplicada es_ES
dc.description.bibliographicCitation Espinosa, M.; Blay, G.; Cardona, L.; Muñoz Roca, MDC.; Pedro, JR. (2017). Catalytic Asymmetric Formal [3+2] Cycloaddition of 2-Isocyanatomalonate Esters and Unsaturated Imines: Synthesis of Highly Substituted Chiral g-Lactams. Chemistry - A European Journal. 23(59):14707-14711. https://doi.org/10.1002/chem.201702777 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1002/chem.201702777 es_ES
dc.description.upvformatpinicio 14707 es_ES
dc.description.upvformatpfin 14711 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 23 es_ES
dc.description.issue 59 es_ES
dc.identifier.pmid 28845883 es_ES
dc.relation.pasarela S\351187 es_ES
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Ministerio de Economía y Competitividad es_ES


This item appears in the following Collection(s)

Show simple item record