16535-89-0Relevant articles and documents
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.
Photochemical Hydrolysis of o-Acetylphenylacetonitriles
Lu, Qingyi,Bovonsombat, Pakorn,Agosta, William C.
, p. 8941 - 8944 (2007/10/02)
Irradiation of 1 and its methyl derivative 10a (λ>280 nm) in methanol leads to photohydrolysis of the nitrile group and formation of the related ketal amides 3 and 11a, respectively.Similar treatment of the dimethyl derivative 10b and of the parent nitrile 13 fails to yield corresponding products of hydrolysis.A mechanism is proposed for these novel hydrolyses.
Synthesis and Characterisation of the Sodium and Lithium Cryptates of Macrobicyclic Ligands Incorporating Pyridine, Bipyridine, and Biisoquinoline Units
Alpha, Beatrice,Anklam, Elke,Deschenaux, Robert,Lehn, Jean-Marie,Pietraskiewicz, Marek
, p. 1042 - 1052 (2007/10/02)
Synthetic procedures have been developed for the preparation of sodium and lithium cryptates of the macrobicyclic ligands 1-11 containing pyridine, bipyridine, and biisoquinoline groups.They involve stepwise construction of the bicyclic system as well as direct macrobicyclisation procedures (Scheme 1) and give access to both symmetrical and dissymmetrical structures.Marked cation template effects have been found that facilitate the cyclisation processes.The ligands 1-11 were isolated as their cryptates with Na+ or Li+ cations.
