114818-52-9Relevant articles and documents
Dynamic Kinetic Asymmetric Reductive Amination: Synthesis of Chiral Primary β-Amino Lactams
Lou, Yazhou,Hu, Yutao,Lu, Jiaxiang,Guan, Fanfu,Gong, Gelin,Yin, Qin,Zhang, Xumu
supporting information, p. 14193 - 14197 (2018/10/15)
A highly efficient ruthenium-catalyzed asymmetric reductive amination (ARA) of racemic β-keto lactams with molecular hydrogen and ammonium salts is disclosed for the synthesis of enantiomerically pure primary amino lactams through dynamic kinetic resolution (DKR). By this approach, a range of syn primary β-amino lactams were obtained in high yields with high chemo-, enantio-, and diastereoselectivity (up to 98 % yield, 99 % ee, >20:1 d.r., syn products). The utility of the products has been demonstrated by rapid access to a key synthetic intermediate towards biologically active drug molecules. Meanwhile, mechanistic studies and control experiments indicate that the reaction may proceed through the hydrogenation of an iminium intermediate.
Enantioselective hydrogenation of tiglic acid in methanol and in dense carbon dioxide catalyzed by a ruthenium-BINAP complex substituted with OCF 3 groups
Dong, Xing,Erkey, Can
, p. 73 - 81 (2008/10/09)
A fluorinated analog of the 2,2′-bis(diphenylphosphino)-1,1′- binaphthyl (BINAP) ligand was synthesized with OCF3-substitution of the aryl groups in BINAP skeleton (p-OCF3-BINAP). Ruthenium complexes of both BINAP (Ru-BINAP) and (p-OCF3)-BINAP (Ru-[(p-OCF3)-BINAP]) were also synthesized and investigated as catalysts for hydrogenation of tiglic acid in methanol. Typically, Ru-[(p-OCF3)-BINAP] had lower activity but had higher enantioselectivity at high hydrogen pressures than Ru-BINAP at the same condition. The effect of OCF3 groups on the catalytic properties was discussed on the basis of NMR spectra and kinetic data. Ru-[(p-OCF 3)-BINAP] was found to have sufficiently high solubility in dense CO2 for homogeneous catalytic reactions and was investigated for hydrogenation of tiglic acid in CO2. The results showed that CO 2 had a great influence on both activity and enantioselectivity. Addition of methanol to CO2 was found to increase the enantioselectivity.