Synthesis of enantiomerically pure 1,2,3,4-tetrahydro-beta-carbolines and N-acyl-1-aryl ethylamines by rhodium-catalyzed hydrogenation.
The rhodium-catalyzed asymmetric hydrogenation of different enamides, in particular, dihydro-beta-carboline derivates, was investigated in the presence of chiral phosphorus ligands. Enantioselectivities of up to 99 % ee were obtained after ligand screening and optimization of the reaction conditions. The scope and limitation of the catalysts were shown in the synthesis of optically active tetrahydro-beta-carbolines and other benchmark N-acyl-1-aryl ethylamines.
Enthaler
Stephan
S
Leibniz-Institut für Katalyse an der Universität Rostock e. V. Albert-Einstein-Str. 29A, D-18059 Rostock, Germany.
Erre
Giulia
G
Junge
Kathrin
K
Addis
Daniele
D
Kadyrov
Renat
R
Beller
Matthias
M
D002243:Carbolines / Q000138:chemical synthesis*; D002384:Catalysis; D005021:Ethylamines / Q000138:chemical synthesis*; D006865:Hydrogenation; D008024:Ligands; D012238:Rhodium; D013237:Stereoisomerism
D002243:Carbolines; D005021:Ethylamines; D008024:Ligands; D012238:Rhodium