ORGN 28 |
| In Mitsunobu oxidation-reduction condensation reactions diethyl azodicarboxylate (DEAD) serves as an oxidant and triphenylphosphine functions as a reductant. We have examined the use of dimethyl mesoxalate (DMM) as a replacement oxidant for DEAD in such reactions and have found that this activated ketone is useful with most alcohol/pro-nucleophile combinations examined. The polarities of the hydrate of DMM and its reduced by-product make it a good alternative when the use of an azo reagent inhibits product isolation in Mitsunobu reactions. |
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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 |