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Stereoselective Synthesis of Phosphoranyl Aryloxiranes through the Addition of a Nucleophilic Stable Carbene to Aromatic Aldehydes

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journal contribution
posted on 06.09.2003, 00:00 by Ona Illa, Heinz Gornitzka, Antoine Baceiredo, Guy Bertrand, Vicenç Branchadell, Rosa M. Ortuño
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.