Stereoselective synthesis of phosphoranyl aryloxiranes through the addition of a nucleophilic stable carbene to aromatic aldehydes

Ona Illa, Heinz Gornitzka, Antoine Baceiredo, Guy Bertrand, Vicenç Branchadell, Rosa M. Ortuño

Producción científica: Contribución a una revistaArtículoInvestigaciónrevisión exhaustiva

22 Citas (Scopus)

Resumen

The [2+1] addition of the stable (phosphanyl)(silyl)carbene 1 to aromatic aldehydes affords phosphoranyl aryloxiranes, a new class of polyfunctional epoxides, in high yields and excellent diastereoselectivity. No reaction is observed for aldehydes bearing strongly electron-donating groups. Theoretical calculations show a good correlation between Gibbs activation energy and the electronic nature of the substituent on the phenyl ring.
Idioma originalInglés
Páginas (desde-hasta)7707-7710
PublicaciónJournal of Organic Chemistry
Volumen68
N.º20
DOI
EstadoPublicada - 3 oct 2003

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