The rearrangemnt of N-acyl-2-furylamines to N-acyl-3-piperidinones (the "aza-Achmatowicz" reaction) is a novel, practical method for enantioselective preparation of nitrogenous substances. A key step in the technique is the chemoenzymatic resolution of racemic furylglycine and furylalanine. The resolved aminoacids are efficiently transformed into building blocks for the synthesis of structures as diverse as azasaccharides, beta-lactams, unusual aminoacids, glycoside antibiotics, and amphibian alkaloids. %%% With this award, the Organic Synthesis Program will support the research of Dr. Marco A. Ciufolini at Rice University. The research explores new ramifications of an old well-established nitrogen heterocycle ring-forming reaction which permits asymmetric control at a crucial stage of the reaction sequence. This is combined with utilization of new organometallic reagents to generate new synthetic methodology that should benefit research in biochemistry, medicine, as well as in the chemical industry.
