Taeboem Oh

EDUCATION

B.S., Juniata College, 1980
Ph.D., University of Virginia, 1985

POSTDOCTORAL APPOINTMENT

University of California, Irvine

COURSES TAUGHT

Chemistry 105, Principles of Chemistry
Chemistry 331, Organic Chemistry I
Chemistry 331L, Organic Chemistry I Laboratory
Chemistry 332, Organic Chemistry II
Chemistry 332L, Organic Chemistry II Laboratory
Chemistry 333, Principles of Organic Chemistry I
Chemistry 333L, Principles of Organic Chemistry I Laboratory
Chemistry 334, Principles of Organic Chemistry II
Chemistry 334L, Principles of Organic Chemistry II Laboratory
Chemistry 531, Survey of Organic Reactions
Chemistry 595C, Synthesis of Natural Products

RESEARCH INTERESTS

Organic Chemistry
Dr. Oh's research is the development of new methods and strategies for organic synthesis. These methods will be applied to undertake efficient syntheses of complex naturally occurring molecules, particularly those with biological activity and potential use in medicine or medical research. One of Dr. Oh's goals is to develop and apply the hetero Diels-Alder reaction to natural product synthesis. The targets of his current interests are indole alkaloids, starting with ergot alkaloids, and histrionicotoxins. Another project involves the development of chiral Lewis acids that can catalyze and induce asymmetry in organic transformations. The emphasis in on transformations that have been shown to be effective in the synthesis of complex natural products.

REPRESENTATIVE PUBLICATIONS

1. "Approaches to Imino diels-Alder Reactions in Imidazolium Ionic Liquids" In Ionic Liquids in Organic Synthesis, ACS Symposium Series 950, Malhotra S. V. Ed. American Chemical Society, Washington, DC, 2007, Chapter 8, 95-103. 
2. "Use of the Intramolecular Heck Reaction for Forming Congested Quaternary Carbon Stereocenters: Stereocontrolled Total Synthesis of (±)-Gelsemine" Madin, A.; O’Donnell, C. J.; Oh, T.; Old, D. W.; Overman, L. E. and Sharp, M. J. Journal of the American Chemical Society (2005) 127, 18054–18065. 
3. "Aza-Cope Rearrangement–Mannich Cyclizations for the Formation of Complex Tricyclic Amines: Stereocontrolled Total Synthesis of (±)-Gelsemine" Earley, W. G.; Jacobsen, J. J.; Madin, A.; Meier, G. P.; O’Donnell, C. J.; Oh, T.; Old, D. W.; Overman L. E. and Sharp, M. J. Journal of the American Chemical Society (2005) 127, 18046–18053. 
4. "Asymmetric Diels-Alder Reactions in Ionic Liquids" Meracz, I. and Oh, T. Tetrahedron Lett. (2003) 44, 6465-6468. 
5. "Simultaneous Coordination of Dimethyl Crotonthioamide by 1,8-Naphthalenediylbis(mercuritrifluoroacetate). Synthesis of Optically Pure 2,2'-Bisboryl-, Bismercuric-, Bissilyl- and Bisstannyl Substituted 1,1'-Binaphthyl Compounds. Catalysis of Diels-Alder Reactions of O-Ethyl Crotonthioate by 2,2'-Bismercuric-1,1'-binaphthalene" Oh, T.; Lopez, P. and Reilly, M. Recent Research Developments in Organic Chemistry, (2002) 6, 379-391. 
6. "Chiral Bidentate Lewis Acids Derived From 1,8-Naphthalenediylbis(dichloroborane) and N-Toluenesulfonyl Amino Acids or Diols", Oh, T. and Reilly, M. Trends in Organic Chemistry (2001) 9, 107-113. 
7. "Recent Advances in Imino Diels-Alder Reactions", Buonora, P.; Olsen, J. C. and Oh, T. Tetrahedron (2001) 57, 6099-6138. 
8. "Synthesis of Optically Pure 2,2'-Bismercuric-1,1'-binaphthyl Compounds: Catalysis of Diels-Alder Reactions of O-Ethyl Crotonthioate", Lopez, P.; Reilly, M. and Oh, T. Eur. J. Org. Chem. (2000), 2901-2903. 
9. "Simultaneous Coordination of Dimethyl Crotonthioamide by 1,8-Naphthalenediylbis(mercurictrifluoroacetate)", Lopez, P. and Oh, T. Tetrahedron Lett. (2000) 41, 2313-2317. 
10. "Total Synthesis of (+)-Gelsemine", Madin, T.; O'Donnell, C.; Oh, T.; Old, D.; Overman, L. and Sharp, M. Angew. Chem. Int. Ed. (1999) 38, 2934-2936. 
11. "1,8-Naphthalenediylbis(dichloroborane) and 1,8-Naphthalenediylbis(mercuric chloride) Compounds as Bidentate Lewis Acids: An NMR Investigation", Lopez, P., Reilly, M. and Oh, T. Recent Developments in Organic Chemistry, Transworld Research Network (1999), 3, 297-309. 
12. "Synthesis of Chiral Non-Racemic Diols From (S,S)-1,2,3,4-Diepoxybutane", Robbins, M. A.; Devine, P. N. and Oh, T. Org. Synth. (1998) 76, 101-109.
13. "Hetero Diels-Alder Reactions of Imines Derived from Cyclohexanones", Pei, H.; Khatchik, I.; Sarkissian, A. and Oh, T. J. Org. Chem. (1998) 63, 4500-4502. 
14. "Hetero Diels-Alder Reaction of Aldimines Derived from 3-Indoleacetaldehyde and 3-Indolecarboxaldehyde", Lin, Y. M. and Oh, T. Tetrahedron Lett. (1997) 38, 727-730. 
15. "Simultaneous Coordination of 2,6-Dimethylpyranone by 1,8-Naphthalenediylbis-(dichloroborane)," Reilly, M. and Oh, T. Tetrahedron Lett. (1995) 36, 217-220. 
16. "Chiral Lewis Acids Derived from 1,8-Naphthalenediylbis(dichloroborane): Mechanistic Aspects," Reilly, M. and Oh, T. Tetrahedron Lett. (1995) 36, 221-224. 
17. "Reagent-Controlled Asymmetric Diels-Alder Reactions," Reilly, M. and Oh, T. Org. Prep. Proced. Int. (1994) 35, 7209. 
18. "Chiral Lewis Acids Derived from 1,8-Naphthalenediylbis(dichloroborane)," Reilly, M. and Oh, T. Tetrahedron Lett. (1994) 35, 7209. 
19. "Factors Influencing the Stereoselectivity in the Cycloaddition of Imino-Dienophiles Derived from Amino Ethers, Amino Alcohols and Amino Acid Esters," Devine, P.N.; Reilly, M. and Oh, T. Tetrahedron Lett. (1993) 34, 5827. 
20. "Asymmetric Diels-Alder Reactions of Carboxylic Ester Dienophiles Promoted by Chiral Lewis Acids," Devine, P.N. and Oh, T. J. Org. Chem.(1992) 57, 396. 
21. "Acyclic Diastereoselection via Claisen Rearrangement with Boron Enolates: Chelation Control of Enolate Geometry," Oh, T.; Wrobel, Z. and Devine, P.N., Syn. Lett. (1992) 81.
22. "Lewis Acid-Catalyzed Diels-Alder Reactions of 3-Methyl-1-Triisopropyl-1,3-Cyclohexadiene: Factors Influencing the Stereoselectivity," Devine, P.N. and Oh, T., J. Org. Chem. (1991) 56, 1955-1958. 
23. "Synthesis of Chiral Nonracemic Diols via Nucleophilic Opening of (S,S)-1,2,3,4-Diepoxybutane," Devine, P.N. and Oh, T., Tetrahedron Lett. (1991) 32, 883-886. 
24. "[2,3]-Wittig Rearrangement of Allylic Glycolate Esters via Boron and Tin Enolates," Oh, T.; Wrobel, Z. and Rubenstein, S.M. Tetrahedron Lett. (1991) 32, 4647.

M. S. THESES

• Room Temperature Ionic Liquids: Interaction with Diels-Alder Substrates and Membranes, (2018) Hossain, I.
• Urea and thiourea catalysts, (2007) Rattanaprasit, O.
• Synthetic methods towards the synthesis of ergot alkaloids (2006) Mecom. J. 
• Synthetic Studies of Aza- and oxa-spirocyclic compounds (2006) Fakhary, Z. 
• Atropisomerism in pyridyl systems (2006) Yulek, C. 
• Binaphthyl Imide Atrope Isomers in Asymmetric Synthesis (2005) Tasu, T. 
• Ionic Liquids in Organic Reactions (2005) Kim, R 
• Studies Directed Toward the Synthesis of Ergoline Alkaloids (2003) Schultz, A. 
• Diels-Alder Reactions in Ionic Liquids (2001) Meracz, I. 
• Binaphthyl Chiral Auxilaries for Conjugate addition (2000) Olsen, J.-C. 
• Novel Approaches to the Synthesis of Azaspirocyclic Compounds (1999) Huang, P. 
• Simultaneous Coordination of Thiocarbonyl Groups by Bidentate Lewis Acids (1999) Lopez, P.