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Synthesis 2000; 2000(7): 980-984
DOI: 10.1055/s-2000-6299
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Tandem Organolithium Addition/Oxa-Bridge Opening of 8-Oxa[3.2.1]bicyclic Pyrone-Alkene Adducts

J. Ramón Rodríguez* , Luis Castedo, José L. Mascareñas
  • *Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, E-15706 Santiago de Compostela, Spain; Fax +34(98)1595012; E-mail: qojoselm@usc.es
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Publication Date:
31 December 2000 (online)

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A novel protocol for opening the bridging ether of 8-oxabicyclic pyrone-alkene adducts is reported. The method relies on the push-pull effect that results from the combined action of an electron-donating enolate and an oxophilic, strong Lewis acid (BF3 · OEt2).

[5 + 2] cycloaddition - alkoxypyrones - ring opening - 8-oxabicyclo[3.2.1]octanes - cycloheptanols - lithium