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

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3 Scopus citations

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.

Original languageEnglish
Pages (from-to)1604-1615
Number of pages12
JournalTetrahedron
Volume71
Issue number10
DOIs
StatePublished - 11 Mar 2015

Keywords

  • Oxyallyl cation
  • Seven-membered carbocycles
  • exo-2-Oxazolidinone dienes

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