ORGN 25 |
| The construction of aziridines and oxiranes represents an extremely useful synthetic transformation for the introduction of functionality into organic molecules. Of the two common disconnections, the sulfur ylide approach offers potential advantages in terms of atom efficiency and facility for stereocontrol. A novel protocol for the generation of sulfur ylides is described. The overall process involves thermal decarboxylation of a carboxymethylsulfonium betaine to give a sulfur ylide which, in the presence of an aldehyde and imine affords the corresponding terminal oxirane and aziridine respectively. Yields were found to correlate with the electron deficiency of the g-acceptor. |
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New Reactions and Methodology
8:00 AM-12:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Rm. R04, Oral
Division of Organic Chemistry |