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Substituting TiCl4 for Ti(O-i-Pr)4 under conditions that are otherwise very similar to those used in Sharpless epoxidation "shuts down" the epoxidation and instead affords selective oxidation of secondary alcohols in the presence of primary alcohols.

Chun-Tin Shei, Hao-Lun Chien, and Kuangsen Sung*; 2008 “TiCl4/t-Butyl Hydroperoxide: Chemioselective Oxidation of Secondary Alcohols and Suppression of Sharpless Epoxidation”, Synlett, 1021-1026.

 

Use of Aldol reaction to create a new C-C bond with two chiral centers

Use of a chiral catalyst to create one out of four stereoisomers

Kinetic resolution with an enzyme

Chen, Yi-Hui; Joly, S.; Huang, Pin-Mei; Sung, Kuangsen*; 2006 “Regio- and Stereo-selectively Kinetic Resolution of Four Stereoisomers of 1-Phenylbutan- 1,3-diol by Candida Rugosa Lipase”, Can. J. Chem., 84, 1031-1035.

 

Three or more compounds react in one pot to form a single product

through several steps.

(1) Sung, Kuangsen*; Chen, Fu-Lin; Huang, Pei-Chun; 2006 “A Modified U-4CR Reaction with 2-Nitrobenzylamine as Ammonia Equivalent”, Synlett, 2667-2669.

(2) Huang, P.-C.; Hsu, G.-J.; Zhuang, B.-R.; Sung, Kuangsen,* 2008 “Novel synthesis of a-PNA monomers by U-4CR”, Amino Acids, 34, 449-453.

(3) Zhuang, Bo-Ren; Hsu, Gien-Jow; Sung, Kuangsen*; 2006 “A Multi-component Reaction to 5-Cyanouracils: Synthesis and Mechanistic Study”, Bioorg. & Med. Chem., 14, 3399-3404.

 

Study of mechanisms of interesting organic reactions through analysis of (1) Hammett linear free-energy relationship, (2) isotope effects, and (3) ab initio calculations

 

(1)   Sung, Kuangsen*; Zhuang, Bo-Ren; Huang, Pin-Mei, Jhong, Sheng-Wei, 2008 “Kinetic and Mechanistic Studies of NEt3-Catalyzed Intramolecular Aminolysis of Carbamate”, J. Org. Chem. 73, 4027-4033.

(2)   Sung, Kuangsen*; Huang, Pin-Mei; Chiang, Shu-Min; 2006 “Kinetic Studies for Amination of Ketenimines: Change of Rate-determining Step by Electron- withdrawing N-Substituents through Electronic Effects”, Tetrahedron, 62, 4795-4799.

(3)   Sung, Kuangsen*; Chen, Fu-Lin; Huang, Pin-Mei; Chiang, Shu-Min; 2006 “Mechanistic Studies of Amination of Ketenimines: Change of Rate-determining Step by N-Substituents through Electronic Effect”, Tetrahedron, 62, 171-181.

(4)   Sung, Kuangsen*; Wu, S.-H.; Wu, R.-R.; Sun, S.-Y.; 2002NMR and ab Initio Studies of Amination of Ketenimine: Direct Evidence for a Mechanism Involving a Vinylidenediamine as an Intermediate”, J. Org. Chem., 67, 4298~4303.

(5)   Sung, Kuangsen*; Wang, Y.-Y.; 2003Mn(III)-Based Oxidative Free-Radical Cyclizations of Substituted Allyl a-Methyl-b-ketoesters: Syntheses, DFT Calculations, and Mechanistic Studies”, J. Org. Chem., 68, 2771~2778.

(6)   Sung, Kuangsen*; Chen, Chao-Chih; 2001 “Kinetics and Mechanism of Acid-catalyzed Hydrolysis of Cyclohexyl Isocyanide and pKa Determination of N-cyclohexylnitrilium ion”, Tetrahedran Lett., 42, 4845-4848.

 

Establishment of substituent constants by ab initio calculations

 

(1)   Sung, Kuangsen*; Chen, F.-L.; 2003Establishment of Steric Substituent Constants in the Adamantane System by ab Initio Calculations”, Org. Lett., 5, 889~891.

(2)   Sung, Kuangsen*; 2002 Ab Initio Calculations of Field Substituent Parameters and Evaluation of Substituent Parameters through Substituent Effects on Stability of Ketenimines, Isocyanides, and Nitriles”, J. Chem. Soc., Perkin Trans. 2, 1658~1661.

(3)   Sung, Kuangsen*, 2000, “N-Substituent Effects on the Stability of Ketenimines”, J. Chem. Soc., Perkin Trans. 2, 847-852. (SCI)

(4)   Sung, Kuangsen*, 1999, “Substituent Effects on Stability and Isomerization Energies of Isocyanides and Nitriles”, J. Org. Chem.., 64, 8984-8989. (SCI)

(5)   Sung, Kuangsen*, 1999, “Substituent Effects on Stability of Ketenimines”, J. Chem. Soc., Perkin Trans. 2, 1169-1173. (SCI)

 

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