409359-85-9Relevant academic research and scientific papers
Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline-Ruthenium Complex
Li, Jing,Shen, Jiefeng,Xia, Chao,Wang, Yanzhao,Liu, Delong,Zhang, Wanbin
, p. 2122 - 2125 (2016/06/01)
Asymmetric hydrogenation of various α-substituted acrylic acids was carried out using RuPHOX-Ru as a chiral catalyst under 5 bar H2, affording the corresponding chiral α-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to construct bioactive chiral molecules. The asymmetric protocol was successfully applied to an asymmetric synthesis of dihydroartemisinic acid, a key intermediate required for the industrial synthesis of the antimalarial drug artemisinin.
Concise Synthesis of 2-Arylpropanoic Acids and Study of Unprecedented Reduction of 3-Hydroxy-2-arylpropenoic Acid Ethyl Ester to 2-Arylpropenoic Acid Ethyl Ester by BH3·THF
Shahid Islam,Ahmad, Syarhabil,Attu, Mary Rose,Foerstering, F. Holger,Mahmun Hossain
, p. 1273 - 1286 (2015/09/22)
We have developed a concise method of synthesizing racemic arylpropanoic acids, which have been widely used as nonsteroidal anti-inflammatory drugs (NSAIDs). The synthesis involves only four steps from commercially available benzaldehyde. The synthesis incorporates an unprecedented reduction reaction, conversion of 3-hydroxy-2-arylpropenoic acid ethyl ester to 2-arylpropenoic acid ethyl ester by BH3·THF. The reduction reaction has been investigated and optimized.
Synthesis of medium ring heterocycles using an intramolecular Heck reaction
Arnold, Leggy A.,Luo, Wenchen,Guy, R. Kiplin
, p. 3005 - 3007 (2007/10/03)
(Equation Presented) Historically, general convergent syntheses of medium ring heterocycles have been difficult to develop. Herein, we describe the synthesis of five classes of heterocycles: dihydrodibenzo[b,f]azepine, -oxocine, and -thiocine and dibenzo[b,f]azepine and -oxepine using a strategy of alkylation followed by highly selective intramolecular Heck arylation reaction. The hetero-tricyclic compounds were available in only two steps starting from commercially available starting materials.
Synthesis of polysubstituted alkenes by Heck vinylation or Suzuki cross-coupling reactions in the presence of a tetraphosphane-palladium catalyst
Berthiol, Florian,Doucet, Henri,Santelli, Maurice
, p. 1091 - 1096 (2007/10/03)
Through the use of [PdCl(C3H5)]2/cis,cis,cis-1,2,3, 4-tetrakis[(diphenylphosphanyl)methyl]cyclopentane as a catalyst, a range of vinyl bromides undergo Suzuki cross-couplings with arylboronic acids in good yields. Furthermore, the catalyst can be used at low loadings, even for reactions of sterically hindered substrates. Mediated by this catalyst, stilbene and 1,1-diphenylethylene undergo Heck reactions with aryl halides to give triarylethylene derivatives. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Facile synthesis of ethyl 2-arylpropenoates by cross-coupling reaction using electrogenerated highly reactive zinc
Jalil, Aishah A,Kurono, Nobuhito,Tokuda, Masao
, p. 7477 - 7484 (2007/10/03)
Highly reactive zinc metal was prepared by electrolysis of a DMF solution containing naphthalene and a supporting electrolyte in a one-compartment cell fitted with a platinum cathode and a zinc anode. This reactive zinc was used for efficient transformation of ethyl 2-bromoacrylate into the corresponding organozinc compound, which was reacted with various aryl iodides or bromides in the presence of 5 mol% Pd(P(o-Tol)3)2Cl2 to give the corresponding cross-coupling products in high yields. These cross-coupling reactions were successfully applied to a synthesis of the precursor of naproxen and cicloprofen, non-steroidal anti-inflammatory agent.
Facile synthesis of 2-arylpropenoic acid esters by cross-coupling using electrogenerated highly reactive zinc and a palladium catalyst
Jalil,Kurono,Tokuda
, p. 1944 - 1946 (2007/10/03)
Highly reactive zinc metal was prepared by electrolysis of a DMF solution containing naphthalene and a supporting electrolyte in a one-compartment cell fitted with a platinum cathode and a zinc anode. The reaction of this reactive zinc with ethyl 2-bromoacrylate at -20 °C and the following cross-coupling reaction with aryl iodides in the presence of 5 mol% Pd(P(o-Tol)3)2Cl2 at 70 °C gave the corresponding ethyl 2-arylpropenoates in almost quantitative yields.
