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44364-AC1
Sigmatropic Rearrangements of Nitrogen Ylides

Robert E. Gawley, University of Arkansas

During the first 18 months of this grant, we studied the alkylation of N-methyl-2-(tributylstannyl)-piperidines, in order to prepare their N-allyl derivatives. The reaction was found to be highly selective, and provided us several ammonium salts that were used in the next step. Tin-lithium exchange produced lithiated nitrogen ylides that underwent a [2,3]-sigmatropic rearrangement with high degree of selectivity, forming two adjacent stereocenters in the process. The reactions were optimized for solvent, gegenion, and reaction conditions. Our preliminary results were published in July, 2007. Other, more exploratory projects have not yet yielded any useful results.

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