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

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Resum

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 originalEnglish
Pàgines (de-a)7707-7710
RevistaJournal of Organic Chemistry
Volum68
Número20
DOIs
Estat de la publicacióPublicada - 3 d’oct. 2003

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