Synthesis and structural studies of novel fused seven-membered carbocycles derived from exo-2-oxazolidinone dienes through (4+3) cycloadditions

Patricia Alcázar; Indira Cruz; Carlos González-Romero; Erick Cuevas-Yañez; Eduardo Díaz; Joaquín Tamariz; Hugo A. Jiménez-Vázquez; David Corona-Becerril; Rubén A. Toscano; Aydeé Fuentes-Benítes

doi:10.1016/j.tet.2014.12.065

Synthesis and structural studies of novel fused seven-membered carbocycles derived from exo-2-oxazolidinone dienes through (4+3) cycloadditions

Patricia Alcázar, Indira Cruz, Carlos González-Romero, Erick Cuevas-Yañez, Eduardo Díaz, Joaquín Tamariz, Hugo A. Jiménez-Vázquez, David Corona-Becerril, Rubén A. Toscano, Aydeé Fuentes-Benítes

Escuela Nacional de Ciencias Biológicas (ENCB)

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3 Citas (Scopus)

Resumen

A series of novel, fused seven-membered rings were obtained from (4+3) cycloadditions of diverse exo-2-oxazolidinone dienes and an oxyallyl cation. 2D-NMR studies (COSY, NOESY, HMBC, and HSQC) showed that the fused carbocycles were obtained as endo/exo diastereoisomeric mixtures. The structure of the predominant exo diastereoisomer was unambiguously established for one of the analogues by X-ray crystallography. It is noteworthy that for the N-benzyl diene, a highly exo stereoselective cycloaddition took place to afford a single isomer.

Idioma original	Inglés
Páginas (desde-hasta)	1604-1615
Número de páginas	12
Publicación	Tetrahedron
Volumen	71
N.º	10
DOI	https://doi.org/10.1016/j.tet.2014.12.065
Estado	Publicada - 11 mar. 2015

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Alcázar, P., Cruz, I., González-Romero, C., Cuevas-Yañez, E., Díaz, E., Tamariz, J., Jiménez-Vázquez, H. A., Corona-Becerril, D., Toscano, R. A., & Fuentes-Benítes, A. (2015). Synthesis and structural studies of novel fused seven-membered carbocycles derived from exo-2-oxazolidinone dienes through (4+3) cycloadditions. Tetrahedron, 71(10), 1604-1615. https://doi.org/10.1016/j.tet.2014.12.065

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title = "Synthesis and structural studies of novel fused seven-membered carbocycles derived from exo-2-oxazolidinone dienes through (4+3) cycloadditions",

abstract = "A series of novel, fused seven-membered rings were obtained from (4+3) cycloadditions of diverse exo-2-oxazolidinone dienes and an oxyallyl cation. 2D-NMR studies (COSY, NOESY, HMBC, and HSQC) showed that the fused carbocycles were obtained as endo/exo diastereoisomeric mixtures. The structure of the predominant exo diastereoisomer was unambiguously established for one of the analogues by X-ray crystallography. It is noteworthy that for the N-benzyl diene, a highly exo stereoselective cycloaddition took place to afford a single isomer.",

keywords = "Oxyallyl cation, Seven-membered carbocycles, exo-2-Oxazolidinone dienes",

author = "Patricia Alc{\'a}zar and Indira Cruz and Carlos Gonz{\'a}lez-Romero and Erick Cuevas-Ya{\~n}ez and Eduardo D{\'i}az and Joaqu{\'i}n Tamariz and Jim{\'e}nez-V{\'a}zquez, {Hugo A.} and David Corona-Becerril and Toscano, {Rub{\'e}n A.} and Ayde{\'e} Fuentes-Ben{\'i}tes",

year = "2015",

month = mar,

day = "11",

doi = "10.1016/j.tet.2014.12.065",

language = "Ingl{\'e}s",

volume = "71",

pages = "1604--1615",

journal = "Tetrahedron",

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number = "10",

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Alcázar, P, Cruz, I, González-Romero, C, Cuevas-Yañez, E, Díaz, E, Tamariz, J , Jiménez-Vázquez, HA, Corona-Becerril, D, Toscano, RA & Fuentes-Benítes, A 2015, 'Synthesis and structural studies of novel fused seven-membered carbocycles derived from exo-2-oxazolidinone dienes through (4+3) cycloadditions', Tetrahedron, vol. 71, n.º 10, pp. 1604-1615. https://doi.org/10.1016/j.tet.2014.12.065

TY - JOUR

T1 - Synthesis and structural studies of novel fused seven-membered carbocycles derived from exo-2-oxazolidinone dienes through (4+3) cycloadditions

AU - Alcázar, Patricia

AU - Cruz, Indira

AU - González-Romero, Carlos

AU - Cuevas-Yañez, Erick

AU - Díaz, Eduardo

AU - Tamariz, Joaquín

AU - Jiménez-Vázquez, Hugo A.

AU - Corona-Becerril, David

AU - Toscano, Rubén A.

AU - Fuentes-Benítes, Aydeé

PY - 2015/3/11

Y1 - 2015/3/11

N2 - A series of novel, fused seven-membered rings were obtained from (4+3) cycloadditions of diverse exo-2-oxazolidinone dienes and an oxyallyl cation. 2D-NMR studies (COSY, NOESY, HMBC, and HSQC) showed that the fused carbocycles were obtained as endo/exo diastereoisomeric mixtures. The structure of the predominant exo diastereoisomer was unambiguously established for one of the analogues by X-ray crystallography. It is noteworthy that for the N-benzyl diene, a highly exo stereoselective cycloaddition took place to afford a single isomer.

AB - A series of novel, fused seven-membered rings were obtained from (4+3) cycloadditions of diverse exo-2-oxazolidinone dienes and an oxyallyl cation. 2D-NMR studies (COSY, NOESY, HMBC, and HSQC) showed that the fused carbocycles were obtained as endo/exo diastereoisomeric mixtures. The structure of the predominant exo diastereoisomer was unambiguously established for one of the analogues by X-ray crystallography. It is noteworthy that for the N-benzyl diene, a highly exo stereoselective cycloaddition took place to afford a single isomer.

KW - Oxyallyl cation

KW - Seven-membered carbocycles

KW - exo-2-Oxazolidinone dienes

UR - http://www.scopus.com/inward/record.url?scp=84923108118&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2014.12.065

DO - 10.1016/j.tet.2014.12.065

M3 - Artículo

SN - 0040-4020

VL - 71

SP - 1604

EP - 1615

JO - Tetrahedron

JF - Tetrahedron

IS - 10

ER -

Synthesis and structural studies of novel fused seven-membered carbocycles derived from exo-2-oxazolidinone dienes through (4+3) cycloadditions

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