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
N1 - Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.
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 -