501355-25-5Relevant articles and documents
Synthesis and characterization of n-substituted (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamides and thioamides as organocatalysts for asymmetric aldol reaction
Androvic, Ladislav,Drabina, Pavel,Panov, Illia,Harmand, Lydie,Padelkova, Zdenka,Sedlak, Milos
, p. 1844 - 1859 (2014/08/18)
In this paper, the preparation and characterization of eight optically pure N-functionalized (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamides and thioamides is described. The prepared amides and thioamides were tested as organocatalysts of aldol reaction of 4-nitrobenzaldehyde and acetone. The highest ee of formation of 4-hydroxy-4-(4-nitrophenyl)butan-2-one was obtained with (S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide (77% ee). The observed deceleration of the aldol reaction catalyzed in this way, as compared with that catalyzed with (S)-proline, was attributed to the formation of little reactive cyclic intermediate, which was isolated and characterized.
New P-stereogenic triaminophosphines and their derivatives: Synthesis, structure, conformational study, and application as chiral ligands
Toselli, Nicolas,Fortrie, Remy,Martin, David,Buono, Gerard
experimental part, p. 1238 - 1245 (2010/11/02)
The synthesis, structural, and conformational studies of new P-chiral triaminophosphines, which feature an indolidine and a 1,2,3,4- tetrahydroquinolidine pattern, respectively, are reported. These compounds can feature very different 3D-structures, although they both could be seen a priori as close derivatives of the previously reported 3-phenyl-1,3-diaza-2- phosphabicyclo[3.3.0]octane. The consequences for the use of such compounds and their derivatives in asymmetric metal-catalysis are discussed on the basis of preliminary results in asymmetric cobalt-catalyzed [6+2] cycloaddition.
Optimized synthesis of tetrahydroisoquinoline-hydantoins
Charton, Julie,Gassiot, Amaury Cazenave,Melnyk, Patricia,Girault-Mizzi, Sophie,Sergheraert, Christian
, p. 7081 - 7085 (2007/10/03)
Several methods have been developed and compared for the solution synthesis of tetrahydroisoquinoline-hydantoin derivatives. The best yields were obtained when the imidazolidine-2,4-dione ring was synthesized in two steps: (1) reaction of Tic-OH with the appropriate amine and (2) cyclization with 1,1′-carbonyldiimidazole.