26618-70-2Relevant articles and documents
Study of the mechanism of ethylene oxidation by palladium(II) complexes containing nitro and/or nitrato ligands in chloroform
Beck,Gusevskaya,Stepanov,Likholobov,Nekipelov,Yermakov,Zamaraev
, p. 167 - 179 (1989)
Complexes of Pd(NOn)2-mCLmL2 (where n = 2, 3; m = 0, 1, 2; L = CH3CN, CD3CN) were synthesized and their reactivities towards ethylene and propylene oxidation in a chloroform medium were investigated. The detailed mechanism of ethylene oxidation by dinitro- and mono-nitrato complexes of palladium in chloroform solutions was studied by IR and 1H NMR spectroscopy. The structures and routes of decomposition of the intermediates to reaction end products are proposed.
Catalytic Asymmetric Reactions of 4-Substituted Indoles with Nitroethene: A Direct Entry to Ergot Alkaloid Structures
Romanini, Simone,Galletti, Emilio,Caruana, Lorenzo,Mazzanti, Andrea,Himo, Fahmi,Santoro, Stefano,Fochi, Mariafrancesca,Bernardi, Luca
, p. 17578 - 17582 (2015)
A domino Friedel-Crafts/nitro-Michael reaction between 4-substituted indoles and nitroethene is presented. The reaction is catalyzed by BINOL-derived phosphoric acid catalysts, and delivers the corresponding 3,4-ring-fused indoles with very good results in terms of yields and diastereo- and enantioselectivities. The tricyclic benzo[cd]indole products bear a nitro group at the right position to serve as precursors of ergot alkaloids, as demonstrated by the formal synthesis of 6,7-secoagroclavine from one of the adducts. DFT calculations suggest that the outcome of the reaction stems from the preferential evolution of a key nitronic acid intermediate through a nucleophilic addition pathway, rather than to the expected "quenching" through protonation.
Asymmetric dearomatization of β-naphthols through a bifunctional-thiourea-catalyzed michael reaction
Wang, Shou-Guo,Liu, Xi-Jia,Zhao, Qun-Chao,Zheng, Chao,Wang, Shao-Bo,You, Shu-Li
, p. 14929 - 14932 (2015)
An intermolecular asymmetric dearomatization reaction of β-naphthols with nitroethylene through a chiral-thiourea-catalyzed Michael reaction is described. Enantioenriched functionalized β-naphthalenones with an all-carbon quaternary stereogenic center could thus be easily constructed from simple naphthol derivatives in good yields and excellent enantioselectivity (up to 79 % yield, 98 % ee). An intermolecular asymmetric dearomatization reaction of β-naphthols with nitroethylene through a chiral-thiourea-catalyzed Michael reaction is described. Enantioenriched functionalized β-naphthalenones with an all-carbon quaternary stereogenic center were easily constructed in good yields and excellent enantioselectivity (up to 79 % yield, 98 % ee).
Enantioselective catalytic approach to the C23–C28 subunit of 24α-methyl steroids
Yakimchyk, Viktoryia S.,Kazlova, Volha V.,Hurski, Alaksiej L.,Savchenko, Rimma G.,Kostyleva, Svetlana A.,Zhabinskii, Vladimir N.,Khripach, Vladimir A.
supporting information, p. 82 - 90 (2019/05/24)
Enantioselective synthesis of C23–C28 subunit of campestane steroids based on catalytic methods is reported. The synthesis was started from (S)-2-isopropyl-4-nitrobutan-1-ol, which is easily accessible by the reaction between isovaleraldehyde and nitroethylene catalyzed by only 2% of (S)-trimethylsilyldiphenylprolinol. Removal of one “extra” carbon from the nitroalcohol was achieved by Ni-catalyzed hydrodecarboxylation of the redox-active ester intermediate. The synthesized C23–C28 fragment was attached to a steroidal core by Julia-Kocienski reaction of a steroidal aldehyde with metallated C23–C28 sulfone. The obtained product of olefination was easily transformed to a precursor of campesterol and (Z)-22-dehydrocampesterol.
Synthesis of nitroolefins and nitroarenes under mild conditions
Zarei, Mahmoud,Noroozizadeh, Ehsan,Moosavi-Zare, Ahmad R.,Zolfigol, Mohammad A.
, p. 3645 - 3650 (2018/04/14)
1,3-Disulfonic acid imidazolium nitrate {[Dsim]NO3} was prepared and characterized as a new ionic liquid and nitrating agent for the ipso-nitration of various arylboronic acids and nitro-Hunsdiecker reaction of different α,β-unsaturated acids and benzoic acid derivatives, by in situ generation of NO2 to give various nitroarenes and nitroolefins without using any cocatalysts and solvents under mild conditions.
