ORGN 472 |
| Armando Córdova, Henrik Sundén, and Anders Bøgevig. Department of Organic Chemistry, Stockholm University, The Arrhenius Laboratory, Stockholm, 106 91, Sweden |
| Herein, we disclose the unprecedented catalytic alfa-oxidation of unmodified ketones. The reactions proceeded with remarkably high selectivities affording alfa-oxyaminated adducts with >99% ee. The transformations were highly regioselective and unsymmetrical ketones were furnished as a single regioisomer with >99% ee. Furthermore, one-step asymmetric synthesis of protected alfa, alfa’-di-hydroxy ketones with >99% ee was also achieved for the first time. In addition, the proline-catalyzed reaction provides a new stereoselective and very mild entry to either enantiomer of anti- or syn- 1,2 diols. The reactions were readily performed on multi-gram scale furnishing a low-cost entry for valuable chiral compounds. |
|
Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Sci-Mix
Division of Organic Chemistry |