ORGN 330 |
| Homolytic substitutions of sulfides and related moieties are fairly well established reactions. Yet, this process has only been reported once with a more oxidized sulfur function. And this has been limited to sulfoxides. We showed that, in contrast to sulfones, the more oxidized sulfinates and sulfinamides could undergo radical closure to yield the corrsponding cyclic compounds. This unprecendented process has been shown to proceed diastereoselectively and with inversion of configuration at the sulfur atom (as was the case with sulfoxides). The full scope of our reaction, as well as the roles of the tether length, the incipient radical, and the leaving group have been examined and will be presented. Finally, this new methodology has been applied to the synthesis of naturally occurring small sulfur heterocycles, which are present in passion fruit extracts. Analogues can be prepared in a highly versatile way.
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New Reactions and Methodology
8:15 AM-11:55 AM, Tuesday, March 27, 2007 McCormick Place Lakeside -- Room E351, Level 3, Oral
Division of Organic Chemistry |
