The principal goals of this research program entail the discovery of new catalytic asymmetric transformations for organic synthesis. Synthetic reactions under investigation include Claisen rearrangements, Diels-Alder reactions, Friedel-Crafts reactions, and nitro-Mannich reactions. To achieve these goals, rational design and combinatorial approaches will be implemented. Design tools include QSSR modeling to accelerate chiral ligand screening and identify important ligand features. Transition structure calculations will be combined with functionality mapping and database searching to develop new hydrogen bonding catalysts.
New reaction methods and new asymmetric methods will be developed. The resultant technologies will be broadly useful in other contexts thereby facilitating the discovery and generation of new pharmaceutical agents.
|Curto, John M; Dickstein, Joshua S; Berritt, Simon et al. (2014) Asymmetric synthesis of ?-allyl-?-aryl ?-amino acids by tandem alkylation/?-allylation of ?-iminoesters. Org Lett 16:1948-51|
|Curto, John M; Kozlowski, Marisa C (2014) ?-Allyl-?-aryl ?-amino esters in the asymmetric synthesis of acyclic and cyclic amino acid derivatives by alkene metathesis. J Org Chem 79:5359-64|
|Walvoord, Ryan R; Huynh, Phuong N H; Kozlowski, Marisa C (2014) Quantification of electrophilic activation by hydrogen-bonding organocatalysts. J Am Chem Soc 136:16055-65|
|Peacock, Jacob R; Walvoord, Ryan R; Chang, Angela Y et al. (2014) Amino acid-dependent stability of the acyl linkage in aminoacyl-tRNA. RNA 20:758-64|
|Allen, Scott E; Hsieh, Sheng-Ying; Gutierrez, Osvaldo et al. (2014) Concerted amidation of activated esters: reaction path and origins of selectivity in the kinetic resolution of cyclic amines via N-heterocyclic carbenes and hydroxamic acid cocatalyzed acyl transfer. J Am Chem Soc 136:11783-91|
|Chen, Ming Z; Gutierrez, Osvaldo; Smith 3rd, Amos B (2014) Through-bond/through-space anion relay chemistry exploiting vinylepoxides as bifunctional linchpins. Angew Chem Int Ed Engl 53:1279-82|
|Walvoord, Ryan R; Kozlowski, Marisa C (2013) Minimizing the amount of nitromethane in palladium-catalyzed cross-coupling with aryl halides. J Org Chem 78:8859-64|
|Metz, Alison E; Kozlowski, Marisa C (2013) 2-Aryl-2-nitroacetates as central precursors to aryl nitromethanes, ýý-ketoesters, and ýý-amino acids. J Org Chem 78:717-22|
|Dickstein, Joshua S; Curto, John M; Gutierrez, Osvaldo et al. (2013) Mild aromatic palladium-catalyzed protodecarboxylation: kinetic assessment of the decarboxylative palladation and the protodepalladation steps. J Org Chem 78:4744-61|
|Padilla-Salinas, Rosaura; Walvoord, Ryan R; Tcyrulnikov, Sergei et al. (2013) Nitroethylation of vinyl triflates and bromides. Org Lett 15:3966-9|
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