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

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

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dc.contributor.author	Espinosa López, Miguel
dc.contributor.author	Blay Llinares, Gonzalo
dc.contributor.author	Cardona Prósper, María Luz
dc.contributor.author	Muñoz, M. Carmen
dc.contributor.author	Pedro, José Ramón
dc.date.accessioned	2020-09-28T14:36:18Z
dc.date.available	2020-09-28T14:36:18Z
dc.date.issued	2017
dc.identifier.citation	Espinosa López, Miguel Blay Llinares, Gonzalo Cardona Prósper, María Luz Muñoz, M. Carmen Pedro, José Ramón 2017 Catalytic Asymmetric Formal [3+2] Cycloaddition of 2-Isocyanatomalonate Esters and Unsaturated Imines: Synthesis of Highly Substituted Chiral γ‐Lactams Chemistry-A European Journal 23 14707 14711
dc.identifier.uri	https://hdl.handle.net/10550/75671
dc.description.abstract	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 aMg(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.
dc.language.iso	eng
dc.relation.ispartof	Chemistry-A European Journal, 2017, vol. 23, p. 14707-14711
dc.subject	Química orgànica
dc.subject	Catàlisi
dc.title	Catalytic Asymmetric Formal [3+2] Cycloaddition of 2-Isocyanatomalonate Esters and Unsaturated Imines: Synthesis of Highly Substituted Chiral γ‐Lactams
dc.type	journal article	es_ES
dc.date.updated	2020-09-28T14:36:18Z
dc.identifier.doi	10.1002/chem.201702777
dc.identifier.idgrec	120858
dc.rights.accessRights	open access	es_ES