Abstract

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.

Public Health Relevance

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.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM087605-03
Application #
8307995
Study Section
Synthetic and Biological Chemistry B Study Section (SBCB)
Program Officer
Lees, Robert G
Project Start
2010-09-30
Project End
2014-07-31
Budget Start
2012-08-01
Budget End
2014-07-31
Support Year
3
Fiscal Year
2012
Total Cost
$301,114
Indirect Cost
$103,114

  Institution

Name
University of Pennsylvania
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
042250712
City
Philadelphia
State
PA
Country
United States
Zip Code
19104

  Publications

Sha, Sheng-Chun; Tcyrulnikov, Sergei; Li, Minyan et al. (2018) Cation-? Interactions in the Benzylic Arylation of Toluenes with Bimetallic Catalysts. J Am Chem Soc 140:12415-12423
Kang, Houng; Herling, Madison R; Niederer, Kyle A et al. (2018) Enantioselective Vanadium-Catalyzed Oxidative Coupling: Development and Mechanistic Insights. J Org Chem :
Tcyrulnikov, Sergei; Curto, John M; Gilmartin, Philip H et al. (2018) Lewis Acid-Promoted Enantioselective Dearomative Spirocyclizations of Allenes. J Org Chem 83:12207-12212
Qu, Bo; Mangunuru, Hari P R; Tcyrulnikov, Sergei et al. (2018) Enantioselective Synthesis of ?-(Hetero)aryl Piperidines through Asymmetric Hydrogenation of Pyridinium Salts and Its Mechanistic Insights. Org Lett 20:1333-1337
Kim, Byeong-Seon; Gutierrez, Osvaldo; Kozlowski, Marisa C et al. (2018) A Simple Procedure for the Synthesis of ?-Hydroxyallenamides via Homoallenylation of Aldehydes. Adv Synth Catal 360:1426-1432
Hu, Chen; Hong, Gang; He, Yuchen et al. (2018) Lewis Acid-Controlled Regioselective Phosphorylation of 2-Indolylmethanols with Diarylphosphine Oxides: Synthesis of Highly Substituted Indoles. J Org Chem 83:4739-4753
Zatolochnaya, Olga V; Rodríguez, Sonia; Zhang, Yongda et al. (2018) Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution. Chem Sci 9:4505-4510
Gutierrez, Osvaldo; Hendrick, Charles E; Kozlowski, Marisa C (2018) Divergent Reactivity in Pd-Catalyzed [3,3]-Sigmatropic Rearrangement of Allyloxy- and Propargyloxyindoles Revealed by Computation and Experiment. Org Lett 20:6539-6543
Patel, Nitinchandra Dahyabhai; Sieber, Joshua D; Tcyrulnikov, Sergei et al. (2018) Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-ortho-Substituted Biaryl Synthesis. ACS Catal 8:10190-10209
Zou, Yike; Gutierrez, Osvaldo; Sader, Avery C et al. (2017) A Computational Investigation of the Ligand-Controlled Cu-Catalyzed Site-Selective Propargylation and Allenylation of Carbonyl Compounds. Org Lett 19:6064-6067

Showing the most recent 10 out of 41 publications