Olefins provide a most efficient entry to organic compounds with diverse and controllable functionality. The goals of this program are to discover and improve a variety of methods for selective olefin oxidation, including osmium-catalyzed aminohydroxylation and dihydroxylation, rhenium-catalyzed epoxidation, bromine-catalyzed aziridination, and ruthenium tetroxide catalyzed oxidation reactions. Emphasis is placed on catalytic amino hydroxylation in both racemic and enantioselective modes, as this problem presents both the greatest challenges and the great potential rewards for synthetic utility. Preliminary results have provided exciting mechanistic insights in this area. The products of olefin oxidation of greatest importance as synthetic intermediates are high-energy compounds that engage in rapid and selective subsequent transformations. Chief among these are epoxides, aziridines, cyclic sulfates, and episulfonium ions. New methods for the synthesis and manipulation of these intermediates are discussed. The ultimate goal is the development and exploitation of an expanded set of highly reliable reactions for the preparation of organic compounds of use to the exciting disciplines of diversity chemistry and drug discovery.
| Hein, Jason E; Tripp, Jonathan C; Krasnova, Larissa B et al. (2009) Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes. Angew Chem Int Ed Engl 48:8018-21 |
| Kalisiak, Jaroslaw; Sharpless, K Barry; Fokin, Valery V (2008) Efficient synthesis of 2-substituted-1,2,3-triazoles. Org Lett 10:3171-4 |
| Whiting, Matthew; Fokin, Valery V (2006) Copper-catalyzed reaction cascade: direct conversion of alkynes into N-sulfonylazetidin-2-imines. Angew Chem Int Ed Engl 45:3157-61 |
| Cassidy, Michael P; Raushel, Jessica; Fokin, Valery V (2006) Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides. Angew Chem Int Ed Engl 45:3154-7 |
| Krasinski, Antoni; Radic, Zoran; Manetsch, Roman et al. (2005) In situ selection of lead compounds by click chemistry: target-guided optimization of acetylcholinesterase inhibitors. J Am Chem Soc 127:6686-92 |
| Feldman, Alina K; Colasson, Benoit; Sharpless, K Barry et al. (2005) The allylic azide rearrangement: achieving selectivity. J Am Chem Soc 127:13444-5 |
| Wu, Peng; Malkoch, Michael; Hunt, Jasmine N et al. (2005) Multivalent, bifunctional dendrimers prepared by click chemistry. Chem Commun (Camb) :5775-7 |
| Narayan, Sridhar; Muldoon, John; Finn, M G et al. (2005) ""On water"": unique reactivity of organic compounds in aqueous suspension. Angew Chem Int Ed Engl 44:3275-9 |
| Johnson, Steven M; Petrassi, H Michael; Palaninathan, Satheesh K et al. (2005) Bisaryloxime ethers as potent inhibitors of transthyretin amyloid fibril formation. J Med Chem 48:1576-87 |
| Himo, Fahmi; Lovell, Timothy; Hilgraf, Robert et al. (2005) Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates. J Am Chem Soc 127:210-6 |
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