10374-29-5Relevant academic research and scientific papers
One-Pot Synthesis of Enantioenriched β-Amino Secondary Amides via an Enantioselective [4+2] Cycloaddition Reaction of Vinyl Azides with N-Acyl Imines Catalyzed by a Chiral Br?nsted Acid
Chiba, Shunsuke,Kaga, Atsushi,Kikuchi, Jun,Nakanishi, Taishi,Terada, Masahiro
, (2020/06/25)
A catalytic enantioselective synthesis of β-amino secondary amides was achieved using vinyl azides as the enamine-type nucleophile and chiral N-Tf phosphoramide as the chiral Br?nsted acid catalyst through a five-step sequential transformation in one pot.
A convenient one-pot approach to Paclitaxel (Taxol) side chain via 1,3-dipolar cycloaddition of carbonyl ylides and N-benzoylbenzyl imines
Sheng, Jiajun,Chang, Huan,Qian, Yu,Ma, Mingliang,Hu, Wenhao
, p. 2141 - 2144 (2018/05/05)
An efficient cascade approach to α-hydroxy-β-amino acid derivatives is reported, which goes through a 1,3-dipolar cycloaddition of carbonyl ylides and N-benzoylbenzyl imines and followed by hydrolysis under acidic conditions. This is the first example of using N-benzoylbenzyl imine as dipolarophile for 1,3-dipolar cycloaddition with carbonyl ylide, which provides a direct and convenient access for the one-pot synthesis of paclitaxel side chain and its derivatives.
A new reactivity mode for the diazo group: Diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines
Kuznetsov, Alexey,Gulevich, Anton V.,Wink, Donald J.,Gevorgyan, Vladimir
supporting information, p. 9021 - 9025 (2014/09/29)
A novel mode of reactivity for the diazo group, the 1,3-addition of a nucleophile and an electrophile to the diazo group, has been realized in the intramolecular aminoalkylation of β-amino-α-diazoesters to form tetrasubstituted 1,2,3-triazolines. The reaction exhibited a broad scope, good functional group tolerance, and excellent diastereoselectivity. In addition, a new Au-catalyzed intramolecular transannulation reaction of the obtained propargyl triazolines to give pyrroles has been discovered.
Asymmetric synthesis of maraviroc (UK-427,857)
Zhao, Gui-Ling,Lin, Shuangzheng,Korotvicka, Ales,Deiana, Luca,Kullberg, Martin,Cordova, Armando
supporting information; experimental part, p. 2291 - 2298 (2010/12/20)
The asymmetric synthesis of Maraviroc (UK-427,857), a chemochine receptor 5 (CCR-5) receptor antagonist, based on an expeditious organocatalytic enantioselective assembly of the chiral βamino aldehyde key fragment is presented. The reactions were performed on a gram-scale and allow for the rapid construction of new Maraviroc analogues.
Modular synthesis of tetrasubstituted imidazoles and trisubstituted oxazoles by aldimine cross-coupling
Kison, Coralie,Opatz, Till
body text, p. 843 - 845 (2009/06/28)
A study was conducted to demonstrate the synthesis of tetrasubstituted imidazoles and trisubstituted oxazoles by aldimine cross-coupling reaction. The method involved 1,2-addition of easily available deprotonated N-monosubstituted α-aminotitriles to aldim
N-Alkylation of carbamates and amides with alcohols catalyzed by a Cp*Ir complex
Fujita, Ken-ichi,Komatsubara, Atsuo,Yamaguchi, Ryohei
experimental part, p. 3624 - 3628 (2009/09/06)
New atom-economical catalytic systems consisting of [Cp*IrCl2]2/NaOAc (Cp*=pentamethylcyclopentadienyl) for the N-alkylation of carbamates and amides using alcohols as alkylating agents under solvent-free conditions have been developed. For example, the reaction of n-butyl carbamate with benzyl alcohol in the presence of [Cp*IrCl2]2 (5.0 mol % Ir) and NaOAc (5.0 mol %) at 130 °C under the absence of solvent gives n-butyl N-benzylcarbamate in the yield of 94%. The present catalytic system is applicable to not only carbamates but also amides, and only harmless water is produced as co-product.
Pd0/SnII promoted Barbier-type allylation and crotylation of sulfonimines
Roy, Ujjal Kanti,Roy, Sujit
, p. 7177 - 7180 (2008/03/11)
A one-pot Barbier protocol is described for the facile formation of homoallyl sulfonamides from sulfonimines and allyl or crotyl bromide in the presence of SnCl2, and catalytic Pd2(dba)3·CHCl3 at room temperature.
Metal catalyzed multicomponent syntheses of secondary propargylamides and oxazoles from silylimines, acid chlorides, and alkynes
Black, Daniel A.,Arndtsen, Bruce A.
, p. 11317 - 11321 (2007/10/03)
Copper(I) and zinc(II) catalyzed routes to construct secondary propargylamides in one-pot procedures from aldehydes, LiN(TMS)2, acid chlorides, and alkynes are described. This reaction has been subsequently used to provide a one-pot synthesis o
OXIDATION OF N-BENZYLIDENEBENZYLAMINE BY OXYGEN THROUGH THE FORMATION OF A CARBANION
Grigoryan, G. S.,Tovmasyan, V. S.,Malkhasyan, A. Ts.,Martirosyan, G. T.,Beletskaya, I. P.
, p. 1043 - 1046 (2007/10/02)
A study was carried out on the oxidation of the methylene group of N-benzylidenebenzylamine through the formation of a carbanion.The conditions were found for a combined oxidation-reduction process using KOH, O2, solvent, dibenzo-18-crown-6 and NaBH4, in which the oxidation is shifted toward the formation of a hydroxy compound, namely, N-benzylidene-2-hydroxybenzylamine.Oxidation in this system is a convenient preparative method for introducing a hydroxyl group into "acidic" CH bonds.
