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.
Original language | English |
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Pages (from-to) | 7707-7710 |
Journal | Journal of Organic Chemistry |
Volume | 68 |
Issue number | 20 |
DOIs | |
Publication status | Published - 3 Oct 2003 |