493-05-0Relevant articles and documents
Target directed enediyne prodrugs: hER and AhR degradation by a synthetic oxo-enediyne
Jones, Graham B.,Kilgore, Michael W.,Pollenz, Richard S.,Li, Aiwen,Mathews, Jude E.,Wright, Justin M.,Huber, Robert S.,Tate, Patricia L.,Price, Thomas L.,Sticca, Robert P.
, p. 1971 - 1976 (1996)
An efficient route to oxo-enediynes is presented. A simple oxo-enediyne has been synthesized, which cyclizes to give an isochroman. The agent shows cytotoxicity for ER rich breast cancer cells and a model for its mode of action is proposed.
Iridium-Catalyzed Enantioselective Hydrogenation of Oxocarbenium Ions: A Case of Ionic Hydrogenation
Lin, Zhenyang,Sun, Yongjie,Wang, Heng,Wen, Jialin,Yang, Tilong,Zhang, Xumu
supporting information, p. 6108 - 6114 (2020/03/04)
Ionic hydrogenation has not been extensively explored, but is advantageous for challenging substrates such as unsaturated intermediates. Reported here is an iridium-catalyzed hydrogenation of oxocarbenium ions to afford chiral isochromans with high enantioselectivities. A variety of functionalities are compatible with this catalytic system. In the presence of a catalytic amount of the Br?nsted acid HCl, an α-chloroether is generated in situ and subsequentially reduced. Kinetic studies suggest first-order kinetics in the substrate and half-order kinetics in the catalyst. A positive nonlinear effect, together with the half kinetic order, revealed a dimerization of the catalyst. Possible reaction pathways based on the monomeric iridium catalyst were proposed and DFT computational studies revealed an ionic hydrogenation pathway. Chloride abstraction and the cleavage of dihydrogen occur in the same step.
A rhodium-catalysed three-component reaction to access C1-substituted tetrahydroisoquinolines
Zhang, Dan,Liu, Junwen,Kang, Zhenghui,Qiu, Huang,Hu, Wenhao
supporting information, p. 9844 - 9848 (2019/12/05)
A rhodium-catalyzed three-component reaction of diazo compounds, anilines and C,N-cyclic azomethine imines via trapping of transient ammonium ylides was developed. This reaction provided a simple and convenient approach for the synthesis of pharmaceutically intriguing tetrahydroisoquinoline derivatives in moderate to good yields (36-85%) with good diastereoselectivities (up to 95 : 5 dr) under mild reaction conditions.
Enantioselective synthesis of tetrahydroisoquinoline derivatives via chiral-at-metal rhodium complex catalyzed [3+2] cycloaddition
Qurban, Saira,Du, Yu,Gong, Jun,Lin, Shao-Xia,Kang, Qiang
supporting information, p. 249 - 252 (2019/01/04)
An asymmetric [3+2] cycloaddition of C,N-cyclic azomethine imines with α,β-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal rhodium complex has been developed. The corresponding C-1-substituted tetrahydroisoquinoline derivatives were obtained in high yields (>90%) with excellent stereoselectivities (up to 99% ee and >20?:?1 dr). The reaction can be conducted on a gram-scale using a low catalyst loading (0.5 mol%) with high yield and selectivity.