ORGN 627 |
Chiral lactones are important architectures found in a variety of macrolide antibiotic structures. Traditional strategies for generating lactones rely on the coupling of alcohols and carboxylic acids using stoichiometric coupling reagents such as 2,4,6-trichlorobenzoyl chloride/DMAP, ethyl azodicarboxylate/PPh3, DCC and 2-halopyridinium salt. This poster describes a catalytic and atom economical synthesis of lactones directly from aldehydes and ketones. Our approach involves an unpredecedented reduction of ketones to generate chiral lactones in up to 99% ee. The mechanism, scope, and limitations of this process will be discussed. |
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Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster
Division of Organic Chemistry |