ORGN 79 |
| Stephen R. Sieck, Matthew D. McReynolds, and Paul R. Hanson. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr, Lawrence, KS 66045 |
| A ring-closing metathesis (RCM) approach employing the second generation Grubbs catalyst in the formation of cyclic, six-membered enol phosphonamidates analogous to the potent anti-cancer agent cyclophosphamide is described. This strategy initially produced various phosphonamidic monochloridates that were further functionalized to an array of acyclic, enol phosphonamidates. Subsequent treatment with a variety of metathesis catalysts afforded both the desired "ring-closed" product and the cross-metathesis-derived dimer. In order to optimize the formation of the RCM product, the effects of various substitution patterns within the enol phosphonamidates have been probed. Other reaction variables that were examined, included: metathesis catalysts, catalyst loads, reaction concentrations, and solvent. |
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New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster
Sci-Mix
Division of Organic Chemistry |