@phdthesis{oai:oist.repo.nii.ac.jp:00000188,
 author = {张, 冬欣 and ザン, ドンシン and Zhang, Dongxin},
 month = {2017-12-21, 2018-03-14},
 note = {Development of efficient methods for the synthesis of biologically important molecules in safe, atom economical, and environmentally friendly ways is a significant goal of modern organic chemistry. In this thesis, efficient methods using amines as catalysts for functionalization of enolizable ketones and synthesis of potential biofunctional molecules have been developed. First, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was indentified to be an efficient catalyst for fast regioselective aldol reactions. Molecules containing tertiary alcohols were concisely obtained through the aldol reactions. The developed DBU-catalysis was applied for the synthesis of spirooxindoles and trifluoromethyl-substituted alcohols. Although the DBU-catalyzed aldol reactions are not enantioselective, the enantiomerically pure forms of the aldol products derived from β-keto esters were obtained by the resolution of the enamines of the aldol products with a homochiral amine. Second, deuteration studies were carried out to elucidate the mechanism of the regioselective formation of the products in the aldol reactions catalyzed by DBU and to understand the relationship between the carbanion formation and the bond-formation. Finally, enantioselective oxa-hetero-Diels-Alder reaction of enones with aryl trifluoromethyl ketones catalyzed by a novel amine catalyst system was developed. Tetrasubstituted carbon centers bearing a trifluoromethyl group were concisely constructed with the formation of the tetrahydropyranone ring. The hetero-Diels-Alder products were further transformed to various trifluoromethyl-substituted tetrahydropyran derivatives.},
 school = {Okinawa Institute of Science and Technology Graduate University},
 title = {アミン触媒を用いるエノール化可能なケトンの官能基化},
 year = {}
}