76228-02-9Relevant academic research and scientific papers
Zinc metal-promoted nucleophilic addition of nonactivated alkyl iodides to aromatic aldimines in the presence of chlorotrimethylsilane in ethyl acetate-DMI
Iwai, Toshiyuki,Ito, Takatoshi,Mizuno, Takumi,Ishino, Yoshio
, p. 1083 - 1086 (2004)
A variety of aromatic aldimines react with nonactivated alkyl iodides in the presence of zinc powder and a catalytic amount of chlorotrimethylsilane (TMSCl) in ethyl acetate-DMI to afford the corresponding α- alkylbenzylamine derivatives in good to excellent yields.
Chiral bipyridine-annulated bicyclo[3.3.1]nonane N-oxide organocatalysts for stereoselective allylation and hydrosilylation reactions
?eimyt?, Simona,Ston?ius, Sigitas
supporting information, (2020/12/21)
The synthesis of chiral C2-symmetric bis(bipyridine N,N′-dioxide) and bis(bipyridine N-monooxide) derivatives featuring bipyridine-annulated bicyclo[3.3.1]nonane framework is reported. The new Lewis basic bipyridine N,N′-dioxides exhibited good
A versatile catalyst for reductive animation by transfer hydrogenation
Wang, Chao,Pettman, Alan,Basca, John,Xiao, Jianliang
supporting information; experimental part, p. 7548 - 7552 (2010/12/19)
An iridium catalyst enables the reductive amination of carbonyl groups with unprecedented substrate scope, selectivity, and activity using formic acid as the hydrogen source (see scheme) The catalyst system provides significant improvement over commonly used boron hydrides.
Asymmetric reduction of imines with trichlorosilane, catalyzed by sigamide, an amino acid-derived formamide: Scope and limitations
Malkov, Andrei V.,Vrankova, Kvetoslava,Stoncius, Sigitas,Kocovsky, Pavel
experimental part, p. 5839 - 5849 (2009/12/26)
(Chemical Equation Presented) Enantioselective reduction of ketimines 6-10 with trichlorosilane can be catalyzed by the N-methyl valine-derived Lewis-basic formamide (S)-23 (Sigamide) with high enantioselectivity (≤97% ee) and low catalyst loading (1-5 mol %) at room temperature in toluene. The reaction is efficient with ketimines derived from aromatic amines (aniline and anisidine) and aromatic, heteroaromatic, conjugated, and even nonaromatic ketones 1-5, in which the steric difference between the alkyl groups R1 and R 2 is sufficient. Simple nitrogen heteroaromatics (8a,b,d) exhibit low enantioselectivities due to the competing coordination of the reagent but increased steric hindrance in the vicinity of the nitrogen (8c,e) results in a considerable improvement. Cyclic imines 32d-d exhibited low to modest enantioselectivities.
The synthesis of β-lactams via a one-pot Reformatsky reaction of imines promoted by Zn/Cp2TiCl2 (cat.)
Chen, Lei,Zhao, Gang,Ding, Yu
, p. 2611 - 2614 (2007/10/03)
In the presence of Zn/Cp2TiCl2 (cat.) α-bromoacetates, γ-bromocrotonates or α-bromomethylacrylates react with imines in one-pot to form β-lactams, 3-vinyl-β-lactams or α-methylene-γ-lactams, respectively, at room temperature without
Selective synthesis of β-amino esters and β-lactams by rhodium-catalyzed reformatsky-type reaction
Kanai, Kazuo,Wakabayashi, Hitoshi,Honda, Toshio
, p. 47 - 51 (2007/10/03)
β-Amino esters and β-lactams are synthesized selectively from aldimines and ethyl bromoacetate by applying a simply modified rhodium-catalyzed Reformatsky-type reaction.
Chemoselective imino aldol reaction promoted by a cation-exchange resin
Shimizu,Itohara
, p. 1828 - 1830 (2007/10/03)
In the presence of a cation-exchange resin, imino aldol reactions of ketene silyl acetals with imines proceeded smoothly to give β-amino esters in good yields. Chemoselectivity between two kinds of imines and / or nucleophiles was also examined in detail.
Ytterbium(III) triflate catalyzed synthesis of quinoline derivatives from N-arylaldimines and vinyl ethers
Makioka,Shindo,Taniguchi,Takaki,Fujiwara
, p. 801 - 804 (2007/10/02)
[4 + 2] Cycloaddition reaction of N-arylaldimines with vinyl ethers is effectively catalyzed by ytterbium(III) triflate to give quinoline derivatives in good yields. Furthermore, the reaction with silyl enol ethers affords 4-siloxytetrahydroquinolines, whereas an imino aldol reaction takes place in the reaction with ketene silyl acetals.
Formation of 2,3-Dihydro-4(1H)-quinolones and Related Compounds via Fries-type Acid-catalysed Rearrangement of 1-Arylazetidin-2-ones
Kano, Shinzo,Ebata, Tsutomu,Shibuya, Shiroshi
, p. 2105 - 2111 (2007/10/02)
A variety of 1-arylazetidin-2-ones were treated with trifluoroacetic acid under reflux, methanesulphonic acid at 100 deg C, or conc. sulphuric acid to give the corresponding 2,3-dihydro-4(1H)-quinolones via acyl migration and N-CO fission.In the case of 1-(3-substituted phenyl)azetidin-2-ones, two positional isomeric products, 5- and 7-substituted 2,3-dihydro-4(1H)-quinolones were obtained. 4-Methyl, 4-ethoxycarbonyl, and 4-piperidin-2-yl-1-arylazetidin-2-ones and their analogues were also converted into the corresponding 2-substituted 2,3-dihydro-4(1H)-quinolones under acidic conditions.The 3-substituted 1-phenylazetidin-2-ones (36) and (37) were converted into the furoquinoline systems (38) and (40), respectively, by application of this method.
