De Munck, L.; Vila, C.; Muñoz Roca, MDC.; Pedro, JR. (2016). Catalytic Enantioselective Aza-Reformatsky Reaction with Cyclic Imines. Chemistry - A European Journal. 22(49):17590-17594. https://doi.org/10.1002/chem.201604606
Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/78864
Title:
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Catalytic Enantioselective Aza-Reformatsky Reaction with Cyclic Imines
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Author:
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De Munck, Lode
Vila, Carlos
Muñoz Roca, María del Carmen
Pedro, José R.
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UPV Unit:
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Universitat Politècnica de València. Departamento de Física Aplicada - Departament de Física Aplicada
Universitat Politècnica de València. Escuela Técnica Superior de Ingeniería del Diseño - Escola Tècnica Superior d'Enginyeria del Disseny
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Issued date:
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Abstract:
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A catalytic highly enantioselective aza-Reformatsky
reaction with cyclic aldimines and ketimines for the
synthesis of chiral b-amino esters with good yields and excellent
enantioselectivities is reported.Areadily ...[+]
A catalytic highly enantioselective aza-Reformatsky
reaction with cyclic aldimines and ketimines for the
synthesis of chiral b-amino esters with good yields and excellent
enantioselectivities is reported.Areadily available
diaryl prolinol is used as a chiral ligand, ZnMe2 as a zinc
source and ethyl iodoacetate as reagent in the presence
of air atmosphere. The reaction with cyclic ketimines generates
a quaternary stereocenter with excellent levels of
enantioselectivity. Furthermore, five-membered N-sulfonyl
ketimines were used as electrophiles with good enantiomeric
excesses, under the optimized reaction conditions.
Moreover, several chemical transformations were performed
with the chiral b-amino esters.
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Subjects:
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Asymmetric catalysis
,
Cyclic ketimines
,
Reformatsky reaction
,
Zinc
,
Beta-amino ester
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Copyrigths:
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Cerrado |
Source:
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Chemistry - A European Journal. (issn:
0947-6539
) (eissn:
1521-3765
)
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DOI:
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10.1002/chem.201604606
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Publisher:
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Wiley
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Publisher version:
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http://dx.doi.org/10.1002/chem.201604606
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Project ID:
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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./
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Thanks:
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Financial support from the MINECO (Gobierno de Espana; CTQ2013-47494-P). L.D.M. thanks the Generalitat Valenciana for a predoctoral grant. C.V. thanks MINECO for a JdC contract. Access to NMR, MS and X-ray facilities from ...[+]
Financial support from the MINECO (Gobierno de Espana; CTQ2013-47494-P). L.D.M. thanks the Generalitat Valenciana for a predoctoral grant. C.V. thanks MINECO for a JdC contract. Access to NMR, MS and X-ray facilities from the Servei central de suport a la investigacio experimental (SCSIE)-UV is also acknowledged.
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Type:
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Artículo
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