ORGN 374 |
| A new chiral Bis-Hydroxamic Acid (BHA)-Molybdenum complex performs catalytic asymmetric oxidation of olefins and sulfides. The use of achiral oxidants with molybdenum catalyst in air at room temperature can tolerate a range of terminal, cis-, and tri-substituted olefins that can provide good to excellent selectivity and yields. Furthermore, this approach oxidizes the most electron rich alkene in the presence of multiple double bonds, by the direct oxidation of myrcene and squalene. In addition to oxidation of olefins, this method utilizes one equivalent of alkyl peroxide to oxidize sulfides in air with yields up to 83% and ee up to 86%. An extension of our methodology combines the asymmetric oxidation with kinetic resolution providing excellent enantioselectivity (ee 92-99%). |
|
Asymmetric Reactions and Syntheses
1:00 PM-5:00 PM, Tuesday, March 27, 2007 McCormick Place East -- Room E351, Level 3, Oral
Division of Organic Chemistry |