1601356-74-4Relevant academic research and scientific papers
Ruthenium(II)/chiral Bronsted acid co-catalyzed enantioselective four-component reaction/cascade aza-michael addition for efficient construction of 1,3,4-tetrasubstituted tetrahydroisoquinolines
Jiang, Jun,Ma, Xiaochu,Ji, Changge,Guo, Zhenqiu,Shi, Taoda,Liu, Shunying,Hu, Wenhao
, p. 1505 - 1509 (2014)
An elegant synergistic catalytic system comprising a ruthenium complex with a chiral Bronsted acid was developed for a four-component Mannich/cascade aza-Michael reaction. The ruthenium-associated ammonium ylides successfully trapped with in situ generated imines indicates a stepwise process of proton transfer in the ruthenium-catalyzed carbenoid Ni￡H insertion reaction. The different decomposition abilities of various ruthenium complexes towards diazo compounds were well explained by the calculated thermodynamic data. The transformation features a mild, rapid, and efficient method for the synthesis of enantiomerically pure 1,3,4-tetrasubstituted tetrahydroquinolines bearing a quaternary stereogenic carbon center from simple starting precursors in moderate yields with high diastereo- and enantioselectivity. An elegant synergistic catalytic system comprising a ruthenium complex with a chiral Bronsted acid was developed for a four-component Mannich/cascade aza-Michael reaction. The transformation features a mild, rapid, and efficient method for the synthesis of enantiomerically pure 1,3,4-tetrasubstituted tetrahydroquinolines from simple starting precursors in moderate yields with high diastereo- and enantioselectivity (see scheme, Cbz=carbobenzyloxy). Copyright
