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Tricyclic oxonium-directed addition: Regiochemistry and stereochemistry of the electrophilic additions to epoxy cycloalkenols.

✍ Scribed by Eleuterio Alvarez; Eduardo Manta; Julio D Martin; Matias L Rodriguez; Catalina Ruiz-Perez; Dacil Zurita

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 275 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)87844-2

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✦ Synopsis

The regio-and stereochemistry of electrophile-promoted transannular ring expansion of cycle 1,5-and 1,6-epoxyalkenes and cycle trans-1,5bisepoxides were studied. The results are rationalized in terms of tricyclic oxonium intermediates showing the directing ability of oxygen substituents in the regio-and stereocontrol observed.

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