863301-32-0Relevant academic research and scientific papers
Catalytic Asymmetric Synthesis of Chiral 2-Vinylindole Scaffolds by Friedel-Crafts Reaction
Arai, Takayoshi,Tsuchida, Akiko,Miyazaki, Tomoya,Awata, Atsuko
, p. 758 - 761 (2017)
A chiral bis(imidazolidine)pyridine (PyBidine)-Ni(OTf)2 complex smoothly catalyzed an asymmetric Friedel-Crafts reaction of 2-vinylindoles with nitroalkenes to give chiral indoles in a highly enantioselective manner while maintaining the 2-vinyl functionality. The chiral 2-vinylindoles offer unique chiral scaffolds for diverse transformations.
Monodentate n-ligand-directed bifunctional transition-metal catalysis: Highly enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes
Guo, Fengfeng,Lai, Guoyin,Xiong, Shunshun,Wang, Sujing,Wang, Zhiyong
, p. 6438 - 6441 (2010)
[Chemical equation presented] A role beyond base : A highly efficient, asymmetric Friedel - Crafts alkylation of indoles with nitroalkenes is presented that uses simple nitrogen compounds combined with Schiff base zinc(II) complexes as bifunctional cataly
Synthesis of Chiral o -Aminobenzylamines by Stereoselective Addition of Grignard Reagents to N -[(o -Aminophenyl)methylene] sulfinamides
Zhong, Xianqiang,Xiao, Guorong,Zhou, Wei
, p. 1019 - 1023 (2021/04/09)
Chiral o-aminobenzylamines are synthons for many chiral ligands and catalysts that have been widely used in asymmetric synthesis. Here, we report a highly efficient and stereoselective addition of Grignard reagents to N -[(o -aminophenyl)methylene]sulfinamides to give a range of o -aminosulfinylimines in good yields with good to excellent diastereoselectivities.
Enantioselective Friedel-Crafts alkylation of indole with nitroalkenes in the presence of bifunctional squaramide organocatalysts
Dündar, Esra,Tanyeli, Cihangir
, (2021/05/26)
A series of chiral bifunctional quinine and 2-aminoDMAP based squaramide organocatalysts are evaluated in Friedel-Crafts alkylation of indoles with nitroolefins. These 3-substituted indole derivatives are synthesized in the presence of sterically encumber
Asymmetric Ruthenium-Catalyzed Hydrogenation of Terpyridine-Type N-Heteroarenes: Direct Access to Chiral Tridentate Nitrogen Ligands
Li, Chenghao,Pan, Yixiao,Feng, Yu,He, Yan-Mei,Liu, Youran,Fan, Qing-Hua
supporting information, p. 6452 - 6457 (2020/08/24)
The first enantioselective hydrogenation of terpyridine-type N-heteroarenes has been successfully developed by using Ru(diamine) complexes as catalysts, providing partially reduced chiral pyridine-amine-type products in high yield (up to 93%) with excellent diastereo- and enantioselectivity (up to 94:6 dl/meso, > 99% ee). These pyridine-amine-type compounds can be served as a new class of chiral multidentate nitrogen-donor ligands, which were successfully applied to the Cu-catalyzed asymmetric Friedel-Crafts alkylation reaction of indoles with nitroalkenes.
C2-symmetry-removing diphenylamine-type chiral bisoxazoline ligands as well as synthetic method and application thereof
-
Paragraph 051; 0152; 0153; 0154, (2019/10/01)
The invention discloses C2-symmetry-removing diphenylamine-type chiral bisoxazoline ligands represented by a formula 3 shown in the description, a synthetic method of the ligands and an application ofthe ligands in an asymmetric catalytic reaction. Accord
A chiral bicyclic skeleton-tethered bipyridine-Zn(OTf)2 complex as a Lewis acid: Enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes
Venkatanna, Kesa,Yeswanth Kumar, Santhakumar,Karthick, Muthupandi,Padmanaban, Ramanathan,Ramaraj Ramanathan, Chinnasamy
, p. 4077 - 4086 (2019/04/30)
A conformationally rigid chiral bicyclic skeleton tethered bipyridine-Zn(OTf)2 complex facilitated the enantioselective Friedel-Crafts alkylation of indoles with trans-β-nitroarylalkenes in an enantioselective manner at elevated temperature. Indoles reacted smoothly with β-nitroarylalkenes to generate the corresponding 3-(2-nitroalkyl)indoles in good to excellent yields (up to 94%) with moderate to excellent enantioselectivities (up to 91%). The stereochemical outcome of the product from indole and trans-β-nitrostyrene in the presence of the CRCB tethered bipyridine-Zn(OTf)2 complex and the DFT calculation of the CRCB tethered bipyridine-Zn:trans-β-nitrostyrene complex support the si-face attack of indole on trans-β-nitrostyrene.
Electrostatically enhanced phosphoric acids and their applications in asymmetric friedel-crafts alkylations
Ma, Jie,Kass, Steven R.
, p. 11125 - 11134 (2019/09/10)
A series of electrostatically enhanced phosphoric acid catalysts were synthesized and studied. These compounds possess two positively charged N-octylpyridinium or triarylphosphonium ion centers at the 3,3′-positions of the (R)-BINOL backbone to enhance re
Design and synthesis of novel indoline-(thio)urea hybrids
Lafzi, Ferruh,Kilic, Haydar,Tanriver, Gamze,Avc?, ?yküm Naz,Catak, Saron,Saracoglu, Nurullah
, p. 3510 - 3527 (2019/11/14)
A series of novel indoline-(thio)urea were designed and prepared using indoline(s) as a new platform and tested as organocatalysts in the Michael and Morita–Baylis–Hillman reactions. Most of the compounds were found to be very active catalysts although they did not promote the enantioselectivity. As agents for the conversion of thiocarbonyl compounds into carbonyl compounds, potentials of PIFA and DDQ were also displayed. Furthermore, DFT calculations rationalized the experimentally observed non-enantioselectivity of the catalysts.
Highly enantioselective Friedel-Crafts alkylation of: N, N -dialkylanilines with trans -β-nitrostyrene catalyzed by a homochiral metal-organic framework
Tanaka, Koichi,Sakuragi, Kenji,Ozaki, Hiroto,Takada, Yoshiki
supporting information, p. 6328 - 6331 (2018/06/21)
The first enantioselective Friedel-Crafts alkylation of N,N-dialkylanilines with trans-β-nitrostyrene catalyzed by a homochiral metal-organic framework constructed from (R)-2,2′-dihydroxy-1,1′-binaphthyl-6,6′-dicarboxylic acid has been developed. The reac
