ORGN 493 |
| Traditionally, tetraethyl 1,3-bisphosphonoacetone has been treated with excess base and linear dialdehydes to afford macrocyclic dienones in a single reaction. We have been investigating the potential for sequential condensations of this reagent to give first a 1-(diethylphosphono)-3-alken-2-one, and then an unsymettrical 1,4-dien-3-one. The mono-condensation with aromatic aldehydes can be realized in good yields via the dianion of the bisphosphonoacetone, and the second condensation can be effected in moderate yields using excess KHCO 3 in an aqueous tBuOH solvent. Enolizable aldehydes or ketones can be employed if DBU and LiCl are used in place of the strong bases.
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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
Division of Organic Chemistry |
