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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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.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.rights.uri info:eu-repo/semantics/openAccess
dc.source 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.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 info:eu-repo/semantics/article
dc.date.updated 2020-09-28T14:36:18Z
dc.identifier.doi https://doi.org/10.1002/chem.201702777
dc.identifier.idgrec 120858

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