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Título : Green synthesis of 6-cyano-2,2-dimethyl-2-H-1-benzopyran and itssubsequent enantioselective epoxidation
Autor : Romanelli, Gustavo Pablo
Sathicqa, Ángel
Vázquez, Patricia
Villa Holguín, Aída Luz
Alarcón Durango, Edwin Alexis
Grajales González, Edwing Javier
Cubillos Lobo, Jairo Antonio
metadata.dc.subject.*: Síntesis verde;Epoxidación enantioselectiva
Fecha de publicación : 2015
Editorial : Elsevier
Citación : G. P. Romanelli, A. Sathicqa, P. Vázquez, A. L. Villa, E. A. Alarcón Durango, E. J. Grajales González, and J. A. Cubillos Lobo, “Green synthesis of 6-cyano-2,2-dimethyl-2-H-1-benzopyran and itssubsequent enantioselective epoxidation,” J Mol. Catal. A-Chem., vol. 398, pp. 11-16. Mar. 2015. http://dx.doi.org/10.1016/j.molcata.2014.11.027
Resumen : tThe clean synthesis of 6-cyano-2,2-dimethyl-2-H-1-benzopyran epoxide starting from 3-methyl-2-butenal is reported using recyclable catalysts. H4PMo11VO40(PMo11V) and (PyH)3HPMo11VO40(Py3–PMo11V) Keggin-type heteropolyacids were used to synthesize 6-cyano-2,2-dimethyl-2-H-1-benzopyran in two steps with 35% yield. This is an alternative procedure to the traditionalmethodology with pyridine or picoline as catalyst, where 6-cyano-2,2-dimethyl-2-H-1-benzopyran isobtained by condensation of 4-cyanophenol with 1,1-diethoxy-3-methyl-2-butene. The 6-cyano-2,2-dimethyl-2-H-1-benzopyran epoxide was obtained using Jacobsen-type catalysts, and in situ generateddimethyldioxirane (DMD) as oxidizing agent, that in comparison to m-CPBA/4-NMO and NaOCl/4-PPNOdid not degrade the catalyst. In presence of 4-phenylpyridine N-oxide (4-PPNO) at 4◦C, enantioselectiv-ities of 87% for 3S,4S-epoxide and 68% for 3R,4R-epoxide were obtained with the S,S- and R,R-Jacobsencatalysts, respectively. Overall yield was approximately 17% for 3S,4S-epoxide.
URI : http://hdl.handle.net/10495/13117
ISSN : 1381-1169
metadata.dc.identifier.*: G. P. Romanelli, A. Sathicqa, P. Vázquez, A. L. Villa, E. A. Alarcón Durango, E. J. Grajales González, and J. A. Cubillos Lobo, “Green synthesis of 6-cyano-2,2-dimethyl-2-H-1-benzopyran and itssubsequent enantioselective epoxidation,” J Mol. Catal. A-Chem., vol. 398, pp. 11-16. Mar. 2015. http://dx.doi.org/10.1016/j.molcata.2014.11.027
1381-1169
http://hdl.handle.net/10495/13117
http://dx.doi.org/10.1016/j.molcata.2014.11.027
Aparece en las colecciones: CIA (Centro de Investigaciones Ambientales y de Ingeniería)

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