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Listing of Norris Group members

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Monosaccharides

Protected furanoses serve as useful platforms upon which to investigate the intra- and inter-molecular chemistry of an attached carbenoid species. MS students in the group have shown that this chemistry is quite useful for the synthesis of optically active ethers and bicyclic furans. The rigid furanose platform limits the possibilities for intramolecular C-H insertion, thereby leading to stereospecific insertions on D-gluco, D-manno, and D-xylo precursors (Carbohydr. Res. 2008).

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Heterocycles

Following an unexpected discovery in a chiral furanose-based system, suitably substituted azide-diazo precursors are being studied as a general route to various nitrogen heterocycles. Metal-catalyzed diazo decomposition could give access to medium- amd large-sized heterocycles. We have isolated 7- and 14-membered ring heterocycles from sugar- and non-sugar-derived precursors and proved their structures through X-ray crystallography.

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Methodologies

As part of our interest in the use of azides and diazo compounds we have developed several novel methods for azide synthesis. Arylsulfonyl azides are found to safe alternatives to current protocols and we have studied their use in the parallel synthesis of alkyl and acyl azides. These methods are amenable to microwave-assisted synthesis and we have now developed one-pot syntheses of sugar-derived azides from the parent alcohols (Tetrahedron. Lett. 2011).

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Department of Chemistry, Youngstown State University, 1 University Plaza Youngstown, Ohio 44555; Contact: 330-941-1553; pnorris@ysu.edu