Catalytic enantioselective aza-Reformatsky reaction with seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines
Fecha
Autores
Directores
Handle
https://riunet.upv.es/handle/10251/204374
Cita bibliográfica
De Munck, L.; Sukowski, V.; Vila, C.; Muñoz Roca, MDC.; Pedro, JR. (2017). Catalytic enantioselective aza-Reformatsky reaction with seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines. Organic Chemistry Frontiers. 4. https://doi.org/10.1039/c7qo00329c
Titulación
Resumen
[EN] A catalytic enantioselective aza-Reformatsky reaction is reported with cyclic dibenzo[b,f][1,4]oxazepines and ethyl iodoacetate leading to the synthesis of chiral ethyl 2-(10,11-dihydrodibenzo[b,f][1,4]oxazepin-11- yl)acetate derivatives with excellent yields and high enantioselectivities (up to 98% yield and 97 : 3 er) using a readily available diaryl prolinol L4 as the chiral ligand and Me2Zn as the zinc source under an air atmosphere. Furthermore, different transformations were carried out with the corresponding chiral beta-amino esters, preserving in all cases the optical purity.
Palabras clave
Reformatsky reaction, Asymmetric catalysis, Cyclic ketimines, Zinc, Beta-amino ester
ISSN
2052-4110
ISBN
Fuente
Organic Chemistry Frontiers
DOI
10.1039/c7qo00329c
Enlaces relacionados
Agradecimientos
Financial support from the MINECO (Gobierno de España; CTQ2013-47494-P) is gratefully acknowledged. L. M. thanks the Generalitat Valenciana for a predoctoral grant. C. V. thanks MINECO for a JdC contract.