Indiana University Purdue University Indianapolis

Kyungsoo Oh Ph.D.

Associate Professor, Chemistry

Education

B.Sc. University of London, Queen Mary, 1999

Ph.D. University of Sussex, 2002

Postdoctoral Fellow, University of Pennsylvania, 2002-2005

Current Research

The primary research activities in our laboratories are centered on the development of synthetically useful and conceptually novel methodologies, in particular, multiple C-C bond formations through rearrangements and fragmentations.

Our current research programs have three main thrusts: 1) the identification of chiral tertiary N-oxides as reactive oxygen transfer reagents and their application towards asymmetric oxidations: epoxidation, sulfoxidation, and alpha-oxygenation of ketones; 2) the development of an intramolecular [2+2] cycloaddition between alkoxyketeniminium salts and carbonyl functionalities and application towards the synthesis of nucleotide analogs as potential antiviral drug candidates; and 3) the development of an intramolecular cycloaddition of alkenes and 1,3-diradical or zwitterionic species from epoxide cleavage and application towards the synthesis of furanoeremophilane natural products. Biological assays and pharmaceutical profiles of the projected compounds are also investigated through collaborations with biologists in biomedical science departments.

Select Publications

Kim, H.; Rooney, O. R.; Meury, R. P.; Oh, K. “Ambivalent Reactivity Modes of β-Chlorovinyl Ketones: Electrophilic Lithium [3]Cumulenolates from Soft Vinyl Enolization Strategy.” Angew. Chem. Int. Ed. 2013, 52, 8026-8030.

Oh, K. “Chapter 46. Stereoselective Carbon-Sulfur Bond Formation” in Stereoselective Drugs and Natural Products, Andrushko, V.; Andrushko, N., Eds.: Wiley-VCH: Weinheim, Germany, 2013.

Kim, H.; Li, J.-Y.; Oh, K. “A Soft Vinyl Enolization Approach to α-Acylvinyl Anions: Direct Aldol/Aldol Condensation Reactions of (E)-β-Chlorovinyl Ketones.” Angew. Chem. Int. Ed2013, 52, 3736-3740.

Kim, H.; Li, J.-Y.; Oh, K. “Studies on Elimination Pathways of β-Halovinyl Ketones Leading to Allenyl and Propargyl Ketones and Furans under the Action of Mild Bases.” J. Org. Chem. 2012, 77, 11132-11145.

Kim, H. Y.; Li, J.-Y.; Kim, S.; Oh, K. “Stereodivergency in Catalytic Asymmetric Conjugate Addition Reactions of Glycine (Ket)imines.” J. Am. Chem. Soc. 2011, 133, 20750-20753.

K. Oh and J.-Y. Li "A cooperative catalysis approach to the Morita-Baylis-Hillman reaction of aryl vinyl ketones" Synthesis 2011, 1960-1967. (Invited Article for a Special Issue on Organocatalysis)

H. Y. Kim and K. Oh "Highly diastereo- and enantio-selective aldol reaction of methyl α-isocyanoacetate: A cooperative catalysis approach" Org. Lett. 201113, 1306-1309. (Highlighted in Organic Chemistry Portal http://www.organic-chemistry.org/Highlights/2012/27February.shtm)

H. Y. Kim, S. Kim and K. Oh “Orthogonal enantioselectivity approaches using homogeneous and heterogeneous catalyst systems: Friedel-Crafts alkylation of indole” Angew. Chem. Int. Ed. 201049, 4476-4478.

K. Oh, J.-Y. Li. and J. Ryu “Brucine N-oxide catalyzed Morita-Baylis-Hillman reaction: A mechanistic implication of dual catalyst system with proline” Org. Biomol. Chem. 2010, 8, 3015-3024.

H. Y. Kim and K. Oh “Brucine-derived amino alcohol-catalyzed asymmetric Henry reaction: An orthogonal enantioselectivity approach” Org. Lett. 2009, 11, 5682-5685. (Highlighted in Organic Chemistry Portal http://www.organic-chemistry.org/Highlights/2010/26July.shtm)

H. Y. Kim, H.-J. Shih, W. E. Knabe and K. Oh "Reversal of enantioselectivity between the copper(I)- and silver(I)-catalyzed 1,3-dipolar cycloadditions using a brucine-derived amino alcohol ligand" Angew. Chem. Int. Ed. 200948, 7420-7423. (highlighted in Synfacts 200912, 1381 and Organic Chemistry Portal; chosen as the First Editors’ Choice in ChemInform (Number 01/2010-01-117). 

K. Oh and W. E. Knabe “Lewis acid-promoted electron transfer deoxygenation of  epoxides, sulfoxides, and amine N-oxides: The role of low-valent niobium complexes from NbCl5 and Zn" Tetrahedron 2009, 65,  2966-2974.

K. Oh and J. Ryu “Chiral tertiary amine N-oxides in asymmetric epoxidation of α,β-unsaturated ketones” Tetrahedron Lett. 200849, 1935-1938.

K. Oh, H. Kim, F. Cardelli, T. Bwititi and A. M. Martynow “Synthesis of cyclic thioethers through tandem C(sp3)-S and C(sp2)-S bond formations from α,β´-dichloro vinyl ketones” J. Org. Chem. 200873, 2432-2434.

K. Oh “A rapid synthesis of the biotin core through a tandem Michael reaction” Org. Lett. 2007, 9, 2973-2975.

K. Oh “An efficient epimerization of biotin sulfone derivatives to 2-epi-biotin analogs” Tetrahedron Lett. 2007, 48, 3685-3688.

K. Oh "4-Ethylhexahydro-4-methyl-(4S,9aS)-pyrrolo[1,2-d][1,4]thiazepin-5(4H)-one"  In: The Electronic Encyclopedia of Reagents for Organic Synthesis. D. Crich, Ed. John Wiley & Sons Ltd.: Sussex, 2007.

K. Oh "N,N-diethyl-1,3,2-benzodioxaborol-2-amine" In: The Electronic Encyclopedia of Reagents for Organic Synthesis. D. Crich, Ed. John Wiley & Sons Ltd.: Sussex, 2006.

K. Oh "Copper(I) chloride" In: The Electronic Encyclopedia of Reagents for Organic Synthesis. D. Crich, Ed. John Wiley & Sons Ltd.: Sussex, 2006.