ORGN 30 |
| Herein we report that the scope of the samarium(II) iodide-promoted Reformatsky reaction has been expanded to include intermolecular coupling reactions of α-haloketones and aldehydes to form β-hydroxyketones. 1-Bromo- and 1-chloropinacolone and their 1-methyl derivatives were coupled with various alkyl and aryl aldehydes in good to quantitative yields. With the 1-methylpinacolone derivatives, good diastereoselectivity was also observed. Generally, a 1:1 ratio of the starting materials is sufficient for efficient coupling, and the yields of reactions involving highly substituted aldehydes (e.g., pivalaldehyde) were especially high, nearly quantitative in some cases.
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Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Sunday, August 19, 2007 BCEC -- 254 A/B, Oral
Division of Organic Chemistry |
