1448701-59-4Relevant academic research and scientific papers
Enantioselective Synthesis of 1-Aryl-Substituted Tetrahydroisoquinolines Through Ru-Catalyzed Asymmetric Transfer Hydrogenation
Perez, Marc,Wu, Zi,Scalone, Michelangelo,Ayad, Tahar,Ratovelomanana-Vidal, Virginie
, p. 6503 - 6514 (2015/10/19)
A convenient and general asymmetric transfer hydrogenation of a wide array of 1-aryl-3,4-dihydroisoquinoline derivatives using a [RuIICl(η6-benzene)TsDPEN] complex in combination with a 5:2 HCOOH-Et3N azeotropic mixture as a hydrogen source was developed. Under mild reaction conditions, the described catalytic transformation secured a practical synthetic access to the corresponding valuable chiral 1-aryltetrahydroisoquinoline units with high atom economy, a broad substrate scope, high isolated yields (up to 97%) and good to excellent enantioselectivities (up to 99% ee). It was found that the stereochemical outcome of the reaction was strongly influenced by both the structure of the catalyst and the substituents present on the substrate. The synthetic utility of the present protocol has been demonstrated through the asymmetric synthesis of several biologically important alkaloids including the antiepileptic drug agent 1c, as well as (-)-nor-cryptostyline alkaloids I and II.
Ruthenium-catalyzed asymmetric transfer hydrogenation of 1-aryl-substituted dihydroisoquinolines: Access to valuable chiral 1-aryl-tetrahydroisoquinoline scaffolds
Wu, Zi,Perez, Marc,Scalone, Michelangelo,Ayad, Tahar,Ratovelomanana-Vidal, Virginie
supporting information, p. 4925 - 4928 (2013/06/04)
Give me an H! Give me another H! The first general and highly enantioselective Ru-catalyzed transfer hydrogenation of a wide range of 1-aryl-substituted 1,2,3,4-dihydroisoquinolines is described. This atom-economic reaction proceeds under mild conditions,
