17718-19-3Relevant academic research and scientific papers
Enantioselective Synthesis of 4-Allyl Tetrahydroquinolines via Copper(I) Hydride-Catalyzed Hydroallylation of 1,2-Dihydroquinolines
Xu-Xu, Qing-Feng,You, Shu-Li,Zhang, Xiao
supporting information, p. 1530 - 1534 (2020/03/13)
CuCl/(R,R)-Ph-BPE-catalyzed asymmetric hydroallylation of 1,2-dihydroquinolines, prepared from readily available quinolines, was developed. The optically active tetrahydroquinolines (THQs) bearing an allylic functionality at position 4 were obtained in good yields and excellent enantioselectivity. The introduced allylic groups are amenable to diverse transformations, thus offering chances to rapidly expand the THQ libraries.
Mild, Metal-Free Oxidative Ring-Expansion Approach for the Synthesis of Benzo[ b]azepines
Stockerl, Sebastian,Danelzik, Tobias,Piekarski, Dariusz G.,García Manche?o, Olga
supporting information, p. 4535 - 4539 (2019/06/17)
Benzo[b]azepines are important structural motifs for the pharmaceutical industry. However, their syntheses are usually lengthy, involving several steps, transition-metal catalysts, and/or harsh conditions. A novel, general, mild, and metal-free oxidative ring expansion tandem reaction of hydroquinolines with TMSCHN2 as a versatile soft nucleophile to gain access to these valuable compounds in a simple and straightforward manner is presented.
Enantioselective Synthesis of 4-Aminotetrahydroquinolines via 1,2-Reductive Dearomatization of Quinolines and Copper(I) Hydride-Catalyzed Asymmetric Hydroamination
Xu-Xu, Qing-Feng,Zhang, Xiao,You, Shu-Li
supporting information, p. 5357 - 5362 (2019/09/06)
A 1,2-reductive dearomatization of quinolines and copper(II) acetate monohydrate/(R,R)-Ph-BPE/P(p-tolyl)3-catalyzed enantioselective hydroamination sequence was developed, affording diverse 4-amino-1,2,3,4-tetrahydroquinolines with high levels of enantioselectivity in either a stepwise or one-pot fashion. Pleasingly, internal cis-cyclic alkenes, which are challenging substrates in copper hydride-catalyzed enantioselective hydroamination reactions, were transformed efficiently under mild conditions.
Enantioselective Synthesis of Boryl Tetrahydroquinolines via Cu-Catalyzed Hydroboration
Kong, Duanyang,Han, Suna,Zi, Guofu,Hou, Guohua,Zhang, Jiaxin
, p. 1924 - 1932 (2018/02/23)
A Cu-catalyzed regio- and enantioselective hydroboration of 1,2-dihydroquinolines with high yields and excellent enantioselectivities (up to 98% ee) was presented. This method could be applied in the asymmetric synthesis of the important intermediates used in the enantioselective synthesis of the potential agent Sumanirole for the treatment of Parkinson's disease and of the potentially interesting positive inotropic agent (S)-903.
