4209-16-9Relevant academic research and scientific papers
Chiral imine-containing quinoline oxazoline compound and metal complex thereof as well as preparation method and application
-
Paragraph 0137-0142, (2022/01/12)
The invention discloses a chiral imine-containing quinoline oxazoline compound which is high in optical purity and has a structural formula as shown in a formula (1), and discloses a preparation method of the chiral imine-containing quinoline oxazoline compound. The invention also discloses a metal complex obtained by complexing the chiral imine-containing quinoline oxazoline compound and a transition metal salt, wherein the metal complex is shown as a formula (6). The synthetic route is efficient, and the total yield of two steps can reach 85%. The metal complex of the chiral imine-containing quinoline oxazoline compound can be used as a catalyst to catalyze hydrosilylation or hydroboration on a carbon-carbon or carbon heteroatom double bond, and is especially suitable for preparing chiral organic compounds with high regioselectivity and optical selectivity.
Construction of Stable Metal–Organic Framework Platforms Embedding N-Heterocyclic Carbene Metal Complexes for Selective Catalysis
Kim, Hyunyong,Kim, Hyunseok,Kim, Kimoon,Lee, Eunsung
supporting information, p. 18687 - 18697 (2021/12/17)
We report a bottom-up approach to immobilize catalysts into MOFs, including copper halides and gold chloride in a predictable manner. Interestingly, the structures of MOFs bearing NHC metal complexes maintained a similar 4-fold interpenetrated cube. They
Iodine-mediated 1,2-aryl migration of primary benzhydryl amines
Chang, Junbiao,Du, Yangxu,Hao, Wei,Hou, Jiao,Lu, Qing,Yu, Wenquan
supporting information, p. 16223 - 16226 (2021/09/22)
An iodine-mediated 1,2-aryl migration reaction of primary benzhydryl amines under transition metal-free conditions has been achieved. The crude imines generated by this rearrangement reaction can be directly transformed into various aromatic secondary ami
Chiral N-heterocyclic carbene-iridium complexes for asymmetric reduction of prochiral ketimines
Kathuria, Lakshay,Samuelson, Ashoka G.
, (2020/12/28)
Enantioselective reduction of imines to the corresponding chiral secondary amines has been studied using a series of chiral half-sandwich iridium complexes. Chiral N-heterocyclic carbene (NHC) ligands in these complexes were synthesized from readily available, naturally occurring amino acids. Inexpensive phenylsilane was used as a convenient hydrogen donor. Under the optimized conditions, Ir-NHC complexes could reduce ketimines in good yields, albeit with moderate enantiomeric excess (ee). The phenylglycine derived chiral NHC was shown to give the best Ir catalyst and it also gave the maximum ee compared to catalysts prepared from other NHCs in this series. The opposite enantiomer of the reduction product was always obtained while using the Ir complex bearing a valine based NHC. The yields were consistently high with a variety of imine substrates having different steric and electronic demands.
Regioselective Synthesis of Multifunctional Allylic Amines; Access to Ambiphilic Aziridine Scaffolds
McLaughlin, Mark G.,Roberts, Dean D.
supporting information, p. 4463 - 4467 (2021/06/28)
We describe, for the first time, a highly regioselective hydrosilylation of propargylic amines. The reaction utilizes a PtCl2/XantPhos catalyst system to deliver hydrosilanes across the alkyne to afford multifunctional allylic amines in high yields. The reaction is tolerant to a wide variety of functional groups and provides high value intermediates with two distinct functional handles. The synthetic applicability of the reaction has been shown through the synthesis of diverse ambiphilic aziridines.
Synthesis and application of axially chiral biscarbolines with functional N-O and sulfone for 1,2-transfer hydrogenations of ketimines
Xing, Yongfei,Wu, Shijie,Dong, Mengxian,Wang, Jie,Liu, Li,Zhu, Huajie
supporting information, (2019/08/08)
A series of axially chiral biscarboline-based sulfones were synthesized from L-tryptophane and applied for enantioselective 1,2-transfer hydrogenations of ketimines using trichlorosilane. The catalyst 4e, which had a tertiary butyl group, exhibited a good conversion and high enantioselectivities up to 96%ee in the series of reactions.
An efficient proline-based homogeneous organocatalyst with recyclability
Li, Qiang,Li, Yuan,Wang, Jingdong,Lin, Yingjie,Wei, Zhonglin,Duan, Haifeng,Yang, Qingbiao,Bai, Fuquan,Li, Yaoxian
supporting information, p. 827 - 831 (2018/02/03)
In this work, a homogeneous organocatalyst was developed for the asymmetric reduction of imines. This catalyst could be separated by cyclodextrin-modified Fe3O4@SiO2 magnetic nanoparticles and then released back into a fre
Transition-Metal-Free Addition of Acetylenes to Ketimines: the First Base-Catalyzed Ethynylation of the C=N Bond
Bidusenko, Ivan A.,Schmidt, Elena Yu.,Ushakov, Igor A.,Trofimov, Boris A.
supporting information, p. 4845 - 4849 (2018/09/14)
A one-pot transition metal-free synthesis of propargylamines in good to excellent yield from ketone-derived imines and aryl- and hetarylacetylenes in the presence of KOBut/DMSO superbase system (40 °C, 10 min) has been developed. The reaction i
Palladium-catalyzed aerobic oxidative hydroamination of vinylarenes using anilines: A wacker-type amination pathway
Song, Eunsun,Kim, Hun Young,Oh, Kyungsoo
supporting information, p. 5264 - 5267 (2017/11/06)
A palladium-catalyzed intermolecular hydroamination of vinylarene derivatives using anilines has been developed for the first time under aerobic conditions, where the regioselective formation of N-arylketimines is accomplished. The current aerobic oxidative hydroamination pathway of anilines is distinct from that of palladiumcatalyzed hydroamination reactions that proceed to give sec-arylethylamine and arylethylamine derivatives, identifying a longstanding missing reaction pathway, Wacker-type amination, to N-arylketimines using anilines. The ready availability of both starting materials, vinylarenes and anilines, offers an attractive and facile synthetic route to N-arylketimines in good to excellent yields.
Decrypting Transition States by Light: Photoisomerization as a Mechanistic Tool in Br?nsted Acid Catalysis
Renzi, Polyssena,Hioe, Johnny,Gschwind, Ruth M.
supporting information, p. 6752 - 6760 (2017/05/29)
Despite the wide applicability of enantioselective Br?nsted acid catalysis, experimental insight into transition states is very rare, and most of the mechanistic knowledge is gained by theoretical calculations. Here, we present an alternative approach (de
