LOH Teck Peng

Professor
Associate Chair (Research)

Education:B. Eng., M. Eng., Tokyo Institute Of Technology; Ph.D., Harvard University

Major Research Interest: Organic Synthesis

Other Interests:Green Chemistry, Chemical Genetics

Phone: (65) 6513 8475

E-mail: teckpeng@ntu.edu.sg

Webpage:http://www1.spms.ntu.edu.sg/~cbc/cv/teckpeng/index.htm



Research Interest

The central theme of research in my group is organic synthesis. Research activities include green chemistry, asymmetric synthesis, the development of new synthetic methodologies, and total synthesis of architecturally complex organic molecules with interesting biological activities. One of the objectives is to develop new C-C bond formation reactions with predictable control of stereochemistry under very mild and environmentally friendly conditions and then apply them to the synthesis of complex natural products. Another objective is to discover new reactions and concepts through the total synthesis of natural products.

 1. Green Chemistry

My group’s research is directed towards the discovery of new reactions that can be carried out in water or ionic liquids as solvents or reactions done without solvent (solvent-free). The discovery that indium complexes can be used as water-tolerant Lewis acid has opened up opportunity for the discovery of new reactions in water. Please refer to Figure A.

2. New concepts, mechanistic insight and synthetic strategy

Some selected achievements in this area are:

(a) Development of a new method for the synthesis of α-adduct from allylic metals and the proposal of a new mechanistic rationale. (b) A new acyclic stereocontrol model based on remote substituent effect has been discovered. (c) Synthetic manipulation of homoallylic alcohols. (d) Fine tuning of the imine to function as diene or dienophile (e) New method for the construction of optically pure pyrollidine ring containing compounds (f) suppression of “selectivity leakage in some reactions. (g) New intermolecular acetal-initiated polyene cyclization.  Please refer to Figure B.

3. Enantioselective Reactions

In our group, we are interested to develop new asymmetric reactions with the following features: (1) high catalytic turnover (2) if possible, without the use of metal complexes (3) asymmetric reactions that can be carried out in water (4) obtaining optically pure compounds based on “deracemization concept”. (5) development of new Chiral metal complexes (indium, silver, boron, copper, etc) (6) Catalytic asymmetric conjugate addition. Please refer to Figure C.

4. Natural Products Synthesis

The total syntheses of numerous natural products have been accomplished in our group. We have successfully synthesized anisatin and antillatoxin. Please refer to Figure D.

 

 

 


Selected Publications

  1. Enantioselective Cationic Poyene Cyclization vs Enantioselective Carbonyl-Ene Reaction, Zhao YJ, Li B, Tan LJS, Loh T-P*, J. Am. Chem. Soc, 2010, 132(30), 10242-10244

  2. Functionalization of Peptides and Proteins by Mukaiyama Aldol Reaction Alam J., Keller TH, Loh TP*, J. Am. Chem. Soc. 2010, 132(28), 9546-9548

  3.  Palladium-catlyzed Oxime Assisted Intramolecular Dioxygenation of Alkenes with 1 atm of Air as the sole oxidant Zhu MK, Zhao JF, Loh TP*, J. Am. Chem. Soc. 2010, 132(18), 6284-6286

  4. Copper-Catalyzed Rearrangement of Tertiary Amines through Oxidation of Aliphatic C-h bonds in Air or oxygen: Direct Synthesis of alpha-Amino Acetals Tian JS, Loh TP*, Angew. Chem Int. Ed. 2010, 49(45), 8417-8420

  5. Synthesis of Water-tolerant Indium Homoenolate in Aqueous Media and Its application in the Synthesis of 1,4-Dicarbonyl Compounds via Palaldium-Catalyzed Coupling with Acid Chloride Shen ZL, Goh KKK, Cheong HL, Loh TP*, J. Am. Chem. Soc. 2010, 132(45), 15852-15855

  6. Palladium-catalyzed Bisolefination of C-C triple Bonds: A Facile Method for the Synthesis of Naphthalene Derivatives Feng C., Loh T-P*, J. Am. Chem. Soc. 2010, 132(50), 17710-17712