People | Faculty | Scott Nelson
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Scott Nelson Department of Chemistry |
Developing new reaction technology for the rapid and efficient construction of therapeutically relevant compounds forms the cornerstone of our research program. Reaction development efforts focus primarily on devising metal-based catalytic protocols for executing stereoselective bond constructions. Our principle objective is the rapid and economical preparation of optically active small-molecule building blocks that relate directly to the complex stereochemical and structural motifs embedded in natural product target molecules.
Catalysis projects emphasize the design and development of strategic asymmetric C-C bond constructions. The development of catalytic asymmetric aldol addition and Claisen rearrangement reactions have been primary goals in our group. These investigations have culminated in the development of both Lewis acid- and Lewis base-catalyzed acyl halide-aldehyde cyclocondensation (AAC) reactions and asymmetric olefin isomerization-Claisen rearrangement (ICR) reactions. Novel variants of the venerable Diels-Alder cycloaddition and Ireland ester-enolate Claisen rearrangement are currently under development.
Identifying transformations offering considerable value to organic synthesis enterprises is another major focus of our program. Reaction discovery efforts are heavily integrated with our programs in catalysis and total synthesis. This program emphasizes the development of novel transformations that dramatically simplify the construction of specific targets or compound classes.
The total synthesis of stereochemically complex molecules serevs two primary uses in our group. First, target-oriented synthesis provides the impetus for identifying new transformations or reaction startegies that are not currently available, thereby driving our reaction discovery activities. Second, complex molecule synthesis provides a vehicle for critically evaluating our catalysis and reaction development in highly demanding settings.
Awards
Bristol-Myers Squibb Foundation, Award for Synthetic Chemistry (2001); Eli Lilly & Co., Award for Synthetic Organic Chemistry (2002); Chancellorís Distinguished Research Award (2002)
Selected Publications
"Amphidinolide B: Asymmetric Synthesis of a C7-C20 Synthon," Gopalarathnam, A.; Nelson, S. G., Org. Lett., 2006, 8, 7
"Asymmetric Claisen Rearrangements Enabled by Catalytic Asymmetric Di(allyl) Ether Syntheses," Nelson, S. G.; Wang, K., J. Am. Chem. Soc., 2006, 128, 4232
"Catalytic Asymmetric Assembly of Stereodefined Propionate Units: An Enantioselective Total Synthesis of (−)-Pironetin," Nelson, S. G.; Shen, X.; Wasmuth, A. S.; Zhao, J.; Zhu, C., J. Am. Chem. Soc., 2006, 128, 7438
"Tandem Sakurai-Aldol Addition Reactions as a Route to Structurally Complex Carbocycles," Steevens, B. D.; Nelson,S. G., J. Org. Chem., 2005, 70, 4375
"Catalytic Asymmetric Acyl Halide-Aldehyde Cyclocondensation Reactions of Substituted Ketenes," Nelson, S. G.; Zhu, C.; Shen, X., J. Am. Chem. Soc., 2004, 126, 14
"Cinchona Alkaloid-Lewis Acid Catalyst Systems for Effecting Highly Enantioselective Ketene-Aldehyde Cycloadditions," Zhu, C.; Shen, X.; Nelson, S. G., J. Am. Chem. Soc., 2004, 126, 5352
"Catalyzed Olefin Isomerization Leading to Highly Stereoselective Claisen Rearrangements of Aliphatic Allyl Vinyl Ethers," Nelson, S. G.; Bungard, C. J.; Wang, K., J. Am. Chem. Soc., 2003, 125, 13000
"A De Novo Enantioselective Synthesis of (–)-Laulimalide," Nelson, S. G.; Cheung, W. S.; Kassick, A. J.; Hilfiker, M. A., J. Am. Chem. Soc., 2002, 124, 13654