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Título : Efecto del agente oxidante y la quiralidad del catalizador en la epoxidación de R-(+)-limoneno con catalizadores tipo Jacobsen
Otros títulos : Oxidising agent and catalyst chirality effect on epoxidation of R-(+)- Limonene using Jacobsen-type catalysts
Autor : Reyes Calle, Juliana
Cubillos Lobo, Jairo Antonio
Montes de Correa, Consuelo
Villa Holguín, Aída Luz
metadata.dc.subject.*: Diastereoselectividad
Epoxidación
Limoneno
Oxidación
Asimetría
Catalizadores
Catalytic Cycle
Catalysis
Chemistry
Fecha de publicación : 2008
Editorial : Universidad Nacional de Colombia
Citación : J. Reyes-Calle, J. A. Cubillos-Lobo, C. Montes-Correa and A. L. Villa-Holguín, "Efecto del agente oxidante y la quiralidad del catalizador en la epoxidación de R-(+)-limoneno con catalizadores tipo Jacobsen," Rev. Ingeniería e Investigación, vol. 28, no. 2, pp. 37-44, 2008.
Resumen : The oxidising agent effect on R-(+)-Limonene epoxide diastereoselectivity using chiral and achiral Jacobsen’s type catalysts is presented. The type of oxidising agent strongly influences diastereoselectivity. Moderate diastereomeric excesses were achieved in the presence of oxidising agents prepared in situ but in the absence of catalyst (23% for DMD and 29% for O2/pivalaldehyde). Similar diastereomeric excesses were obtained with both chiral and achiral catalyst when the oxidising agents were prepared in situ; 56% and 50% excesses were obtained when using DMD for the chiral and achiral catalyst (respectively) and 38% using O2/pivalaldehyde for both catalysts. Diastereomeric excesses were not observed in the absence of catalyst when using commercial oxidising agents; the chiral catalyst presented larger diastereomeric excesses than its achiral counterpart: 65% and 38% excess using NaOCl for the chiral and achiral catalyst, respectively, and 79% and 39% using m-CPBA for the chiral and achiral catalyst, respectively. This suggests that at least one oxidant species, different from the conventionally accepted (MnV(oxo)), might be involved in this catalytic process. A modification of the traditional catalytic cycle is proposed considering the type of oxidising agent. The catalyst’s chiral centre appears to govern asymmetric induction when commercial oxidising agents are used, whereas the R-(+)-Limonene chiral centre appears to govern asymmetric induction in the presence of in situ-prepared oxidising agents. On the other hand, the chemical stability of Jacobsen’s catalyst improved when in situ produced DMD was used as oxidising agent. Keywords: diastereoselectivity, epoxidation, R-(+)-Limonene, oxidising agent type, asymmetric induction, chiral, achiral.
ISSN : 01205609
22488723 E
Aparece en las colecciones: CIA (Centro de Investigaciones Ambientales y de Ingeniería)

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