A.B. (2001) Bowdoin College, Brunswick, ME
Ph.D. (2007) University of California, Los Angeles, CA
Postdoctoral Fellow (2007-2009) University of California, Los Angeles, CA
Hypercube scholar award (2001)
John Stauffer Fellowship (2006)
Thomas L. and Ruth F. Jacobs Award (2007)
Vicki and Patrick F. Stone Scholar (2011)
Research Group Website:
Organic and Bioorganic Website:
Catalysis based on the fundamentals of natural enzymes and proteins is the new frontier of green and efficient synthesis. Enzymatic acceleration ranges from 105 in Cyclophilin to 1017 in Orotidine monophosphate decarboxylases ("A proficient enzyme." Science 1995, 267, 90-93) The dramatic miniaturization of nature's enzymes into catalytic peptides is a significant achievement in modern synthetic chemistry and biology. Structural preorganization in the transition states is critical for imbuing reactivity and selectivity ("Asymmetric Catalysis Mediated by Synthetic Peptides." Chem. Rev. 2007, 107, 5759-5812). However, these factors are poorly understood for peptide catalysis due to the large size, conformational flexibility and weakness of the interactions responsible for preorganization and transition state stabilization. By quantifying these factors using our strategies and tools, we will begin to create theories that govern the selectivities of these reactions and eventually contribute to the rational design of peptide catalysts.
Our group participates in materials science research as part of the Center for Sustainable Materials Chemistry (CSMC). Our group contributes computational and theoretical expertise to the CSMC research mission, providing a fundamental understanding of aqueous metal hydroxide clusters and translating these discoveries to guide experimental efforts by research groups within the CSMC and beyond. While research in the PHYC group is computational, the ultimate goal is the complete understanding of these metal hydroxide clusters such that computations are no longer necessary to predict experimental outcomes or properties of these clusters.
Our group seeks to apply state-of-the-art computational tools towards the efficient elucidation of mechanisms and factors that control the reactivity and selectivity of complex modern synthetic organic reactions. Unprecedented growth in new computational technologies and theories has made a vast spectrum of synthetic reactions amenable to computational analyses. The ultimate achievement is the complete understanding of the structural and energetic factors responsible for reactivity and selectivity. Our group and others have demonstrated that this is already reality. The same success is rare for chemical transformations where the structures are large, significant conformational flexibility is present, and/or the interactions responsible for the reactivity and selectivity are largely non-covalent and/or weak. Computational analysis of complex synthetic reactions often trail significantly behind experiments, while some are simply intractable. We address these challenges by harnessing software and hardware already in existence as well as developing our own.
- "Electrolytic Synthesis of Aqueous Aluminum Nanoclusters and in sity Characterization by Femtosecond Raman Spectroscopy and Computations,: Wang, W.; Liu, W.; Chang, I-Y.; Wills, L.A.; Zakharov, L. N.; Boettcher, S. W.; Cheong, P. H.-Y.; Fang, C.; KEszler, D. A. Proc. Natl. Acad.Sci. USA 2013, Early Edition Article. DOI: 10.1073/pnas.1315396110
- "Palladium-Catalyzed Completely Linear-Selective Negishi Cross-Couplingof Allylzinc Halides with Aryl and Vinyl Halides," Yang, Y.; Mustard, T. J. L.; Cheong, P. H.-Y.; Buchwald, S. L. Angew. Chem. Int. Ed. 2013, Article Accepted. DOI: 10.1002/anie.201308585
- "Stereocontrol in Asymmetric γ-Lactam Syntheses from Imines and Cyanosuccinic Anhydrides," Pattawong, O.; Tan, D. Q.; Fettinger, J. C.; Shaw, J. T.; Cheong, P. H.-Y. Org. Lett. 2013, Article ASAP. DOI: 10.1021/ol402561q
- "Stereoselective Synthesis of γ-Lactams from Imines and Cyanosuccinic Anhydrides," Tan, D. Q.; Younai, A.; Pattawong, O.; Fettinger, J. C.; Cheong, P. H.-Y.; Shaw, J. T. Org. Lett. 2013, Article ASAP. DOI: 10.1021/ol402554n
- "Identifying Nanoscale M13 Clusters in the Solid State and Aqueous Solution: Vibrational Spectroscopy and Theoretical Studies," Jackson, M. N.; Wills, L. A.; Chang, I.-Y.; Carnes, M. E.; Scatena L. F.; Cheong, P. H.-Y.; Johnson, D. W. Inorg. Chem. 2013, 52 (10), 6187-6192. DOI: 10.1021/ic400611z
- "C-H---O Non-Classial Hydrogen Bonding in the Stereomechanics of Organic Transformations: Theory and Recognition," Johnston, R. C.; Cheong, P. H.-Y. Org. Biomol. Chem. 2013, 11, 5057-5064. DOI: 10.1039/C3OB40828K
- "[Sc2(µ-OH)2(H2O)6(NO3)2](NO3)2: Aqueous Synthesis and Characterization," Wang, W.; Chang, I-Y.; Zakharov, L.; Cheong, P. H.-Y.; Keszler, D. Inorganic Chemistry 2013, 52, 1807-1811. DOI: 10.1021/ic301814z
- "Mechanism and the Origins of Stereospecificity in Copper-Catalyzed Ring Expansion of Vinyl Oxiranes: A Traceless Dual Transition-Metal-Mediated Process," Mustard, T. J. L.; Mack, D. J.; Njardarson, J. T.; Cheong, P. H.-Y. J. Am. Chem. Soc. 2013, 135, 1471–1475. DOI: 10.1021/ja310065z
- "Mechanism and Stereocontrol: Enantioselective Addition of Pyrrole to Ketenes using Planar-Chiral Organocatalysts," Pattawong, O.; Mustard, T. J. L.; Johnston, R. C.; Cheong, P. H.-Y. Angew. Chem. Int. Ed. 2013, 52, 1420-1423. DOI: 10.1002/anie.201208417
- "Synthesis and Computational Analysis of Densely Functionalized Triazoles Using o-Nitrophenylalkynes," McIntosh, M. L.; Johnston, R. C.; Pattawong, O.; Ashburn, B. O.; Naffziger, M. R.; Cheong, P. H.-Y.; Carter, R. G. J. Org. Chem. 2012, 77, 1101–1112. dx.doi.org/10.1021/jo202467k
- "Organocatalytic Kinetic Resolution Cascade Reactions: New Mechanistic and Stereochemical Manifold in Diphenyl Prolinol Silyl Ether Catalysis," McGarraugh, P. G.; Johnston, R. C.; Martínez-Muñoz, A.; Cheong, P. H.-Y.; Brenner-Moyer, S. E. Chem. Eur. J. 2012, 18, 10742–10752. dx.doi.org/10.1002/chem.201104029
- "Mechanism and Stereoselectivity of a Dual Amino-Catalyzed Robinson Annulation: Rare Duumvirate Stereocontrol," Pierce, M. D.; Johnston, R. C.; Mahapatra, S.; Yang, H.; Carter, R. G.; Ha-Yeon Cheong, P. J. Am. Chem. Soc. 2012, 134, 13624–13631. dx.doi.org/10.1021/ja3018219
- "Highly Stereoselective and Scalable anti-Aldol Reactions Using N-(p-Dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: Scope and Origins of Stereoselectivities," Hua Yang, Subham Mahapatra, Paul Ha-Yeon Cheong,* and Rich G. Carter* J. Org. Chem. 2010, 75, 7279–7290. dx.doi.org/10.1021/jo1015008
AB, PhD, and Postdoc
- "Quantum Mechanical Investigations of Organocatalysis: Mechanisms, Reactivities, and Selectivities," Cheong, P. H.-Y.; Legault, C. Y.; Um, J. M.; Çelebi-Ölçüm, N.; Houk, K. N. Chem. Rev. 2011, 111, 5042-137.