Kyungsoo Oh
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.
Recent Publications
K. Oh and J. Ryu "Chiral tertiary amine N-oxides in asymmetric epoxidation of alpha,
beta-unsaturated ketones" Tetrahedron Lett. 2008, 49, in press.
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 dichloro vinyl
ketones" J. Org. Chem. 2008, 73, in press.
K. Oh "A rapid synthesis of 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.
J. D. Winkler and K. Oh “A One-Step Synthesis of 2,3-Dihydro-4H-pyran-4ones from
3-Ethoxy a, ß-Unsaturated Lactones” Org. Lett. 2005, 7, 2421-2423.
J. D. Winkler, K. Oh and S. M. Asselin “Synthesis of Highly Functionalized Furanones
via Aldol Reaction of 3-Silyloxyfurans”
Org. Lett. 2005, 7, 387-389.
K. Oh, D. Cheshire and P. J. Parsons “Studies Towards the Synthesis of Rapamycin:
Regiocontrol in the Addition of Carbanions to Enantiomerically Pure Epoxides and the
Formation of a Highly Substituted Tetrahydrofuran”
SynLett. 2005, 1630-1632.
K. Oh, P. J. Parsons and D. Cheshire “An Efficient Stereoselective Synthesis of
Substituted 1,3-Dienes”
SynLett.
2004, 2771-2775.
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