189816-06-6Relevant articles and documents
AlCl3-promoted three-component cascade reaction for rapid access to [1,2,3]triazolo[5,1-a]isoquinolines
Wu, Yangang,Meng, Yonggang,Liu, Zibo,Zhang, Mengge,Song, Chuanjun
, (2019)
Novel AlCl3-promoted, three component cascade Henry reaction-triazole formation-intramolecular 6-endo-dig cyclization reactions between 2-alkynylaryl aldehydes, nitroalkanes, and sodium azide for the assembly of [1,2,3]triazolo[5,1-a]isoquinolines have been developed. Further transformations of representative [1,2,3]triazolo[5,1-a]isoquinolines are also described.
Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of 1,3-Disubstituted Isoquinolines
Bartberger, Michael D.,Daiger, Martin T.,Grünanger, Christian U.,Kim, Alexia N.,Ngamnithiporn, Aurapat,Stoltz, Brian M.,Virgil, Scott C.,Welin, Eric R.
, p. 3241 - 3248 (2020/03/10)
The development of a general method utilizing a hydroxymethyl directing group for asymmetric hydrogenation of 1,3-disubstituted isoquinolines to provide chiral 1,2,3,4-tetrahydroisoquinolines is reported. The reaction, which utilizes [Ir(cod)Cl]2 and a commercially available chiral xyliphos ligand, proceeds in good yield with high levels of enantioselectivity and diastereoselectivity (up to 95% ee and >20:1 dr) on a range of differentially substituted isoquinolines. Directing-group studies demonstrate that the hydroxymethyl functional group at the C1 position is more efficient at enabling hydrogenation in comparison to other substituents, although high levels of enantioselectivity were conserved across a variety of polar and nonpolar functional groups. By utilization of the generated chiral β-amino alcohol as a functional handle, the synthetic utility is further highlighted via the synthesis of 1,2-fused oxazolidine, oxazolidinone, and morpholinone tetrahydroisoquinolines in one step. Additionally, a non-natural analogue of the tetrahydroprotoberberine alkaloids was successfully synthesized.
