Stereoselective synthesis of phosphoranyl aryloxiranes through the addition of a nucleophilic stable carbene to aromatic aldehydes |
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Authors: | Illa Ona Gornitzka Heinz Baceiredo Antoine Bertrand Guy Branchadell Vicenç Ortuño Rosa M |
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Institution: | Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Barcelona, Spain. |
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Abstract: | 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. |
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