ORGN 494 |
| Conjugate addition of radicals to α,β - unsaturated amides, esters and ketones has been extensively studied, in particular its intramolecular version. However, the intermolecular radical addition to the α,β - disubstituted carbonyls still poses a significant challenge to a synthetic chemist due to their diminished reactivity and, in many cases, poor diastereoselectivity of the addition. Herein we wish to report our progress in developing a methodology towards a diastereoselective intermolecular addition of the oxygen-flanked radicals to α,β - disubstituted unsaturated esters (Fig. 1). This addition allows for generation of three contiguous stereogenic centers. Interestingly, very high levels of diastereoselectivity have been observed for the formation of both α and β stereocenters.
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |
