5033-95-4Relevant academic research and scientific papers
Conjugate addition of aryl nucleophiles to α,β-unsaturated cinnamic acid derivatives containing Evans type chiral auxiliaries
Leitis, Zigmārs,Lūsis, Viesturs
, p. 843 - 851 (2016/09/02)
Cinnamides containing oxazolidin-2-one type auxiliaries have been prepared. A novel pathway to chiral 4-aryl-6-methyl-3,4-dihydrocoumrines via the asymmetric conjugate addition of arylmagnesium bromides to these cinnamides is described.
Modified Yamaguchi reagent: Convenient and efficient esterification
Okuno, Yoshinori,Isomura, Shigeki,Nishibayashi, Akihiro,Hosoi, Aiko,Fukuyama, Kei,Ohba, Masashi,Takeda, Kazuyoshi
supporting information, p. 2854 - 2860 (2014/10/15)
A convenient and efficient esterification method that used a modified Yamaguchi reagent (2,4,6-trichlorobenzoyl chloride-4-dimethylaminopyridine) and avoided use not only of intractable acid chloride but also of acid anhydrides was proposed. The reaction mechanism was described by Fourier transform infrared spectroscopy and supported by a density functional theory calculation.
Antileishmanial lead structures from nature: Analysis of structure-activity relationships of a compound library derived from caffeic acid bornyl ester
Glaser, Jan,Schultheis, Martina,Hazra, Sudipta,Hazra, Banasri,Moll, Heidrun,Schurigt, Uta,Holzgrabe, Ulrike
, p. 1394 - 1410 (2014/03/21)
Bioassay-guided fractionation of a chloroform extract of Valeriana wallichii (V. wallichii) rhizomes lead to the isolation and identification of caffeic acid bornyl ester (1) as the active component against Leishmania major (L. major) promastigotes (IC50 = 48.8 μM). To investigate the structure-activity relationship (SAR), a library of compounds based on 1 was synthesized and tested in vitro against L. major and L. donovani promastigotes, and L. major amastigotes. Cytotoxicity was determined using a murine J774.1 cell line and bone marrow derived macrophages (BMDM). Some compounds showed antileishmanial activity in the concentration range of pentamidine and miltefosine which are the standard drugs in use. In the L. major amastigote assay compounds 15, 19 and 20 showed good activity with relatively low cytotoxicity against BMDM, resulting in acceptable selectivity indices. Molecules with adjacent phenolic hydroxyl groups exhibited elevated cytotoxicity against murine cell lines J774.1 and BMDM. The Michael system seems not to be essential for antileishmanial activity. Based on the results compound 27 can be regarded as new lead structure for further structure optimization.
Widely useful DMAP-catalyzed esterification under auxiliary base- and solvent-free conditions
Sakakura, Akira,Kawajiri, Kimio,Ohkubo, Takuro,Kosugi, Yuji,Ishihara, Kazuaki
, p. 14775 - 14779 (2008/09/17)
With regard to atom economy and E-factor, catalytic condensation of carboxylic acids with equimolar amounts of alcohols is the most desirable. Although several highly active dehydration catalysts have been reported, more efficient alternatives are still strongly needed because the dehydrative esterification of tertiary alcohols, phenols, acid-sensitive alcohols, amino acids, and hardly soluble alcohols has never proceeded satisfactorily. Here we report new insights into the classical DMAP-catalyzed acylation of alcohols: surprisingly, only a 0.05-2 mol % of DMAP can efficiently promote acylation of alcohols with acid anhydrides under auxiliary base- and solvent-free conditions to give the corresponding esters in high yields. Furthermore, we achieved the recovery and reuse of commercially available polystyrene-supported DMAP without using any solvents. These serendipitous findings provide widely useful and environmentally benign esterification methods, which might be more practical and reliable than catalytic dehydrative condensation methods, in particular, for the less reactive alcohols which hardly condense with carboxylic acid directly.
Highly diastereoselective synthesis of vinylcyclopropane derivatives with (-)-8-phenylmenthol as chiral auxiliary
Ye,Tang,Dai
, p. 5717 - 5722 (2007/10/03)
The silylated telluronium allylide 4, generated in situ from the corresponding telluronium salt in the presence of LiTMP, reacted with (-)-8-phenylmenthyl α,β-unsaturated esters to afford trans-2-silylvinyl-trans-3-substituted cyclopropyl esters with high diastereoselectivity in high yields. The absolute configuration was determined by chemical transformation. A mechanistic rationale is proposed.
Electro-organic reactions. Part 42. The diastereoselective cathodic hydrodimerisation of cynnamate esters; preparative aspects
Utley, James H. P.,Guellue, Mustafa,Motevalli, Majid
, p. 1961 - 1970 (2007/10/02)
The cathodic reduction of cinnamate esters formed with chiral alcohols proceeds smoothly via coupling and intramolecular condensation, with high stereoselectivity, to give good yields of diastereoisomeric mixtures of the esters of the all-trans (+/-)-2-ca
REACTION OF BENZYLIDENEBENZYLAMINE WITH CINNAMIC ACID DERIVATIVES UNDER CONDITIONS OF PHASE-TRANSFER CATALYSIS. I. SYNTHESIS OF β-ARYL-γ-PHENYL-γ-AMINOBUTYRIC ACIDS AND THEIR DERIVATIVES
Potapov, V. M.,Gracheva, R. A.,Sivov, N. A.,Savina, S. A.,Sivova, L. A.
, p. 1694 - 1699 (2007/10/02)
The reaction of benzylidenebenzylamine with the esters of substituted cinnamic acids under the conditions of phase-transfer catalysis gives high yields of β-aryl-γ-phenyl-γ-aminobutyric acids and their derivatives (hydrochlorides, 4-aryl-5-phenyl-2-pyrrolidones).
Reaction of Chiral Lithium Diorganocopper Reagents, LiRR*Cu, with α,β-Unsaturated Esters of Chiral Alcohols
Gustafsson, Bill,Hansson, Anna-Tora,Ullenius, Christina
, p. 113 - 118 (2007/10/02)
Conjugate addition of organometallic reagents to chiral esters of trans-3-phenyl-2-propenoic or trans-2-butenoic acid has been studied.The reagents were PhMgBr, LiPh2Cu, LiMe2Cu, LiMeR*Cu, and LiPhR*Cu.The chiral ligand R* was the 2-(1-dimethylaminoethyl)phenyl group.The assymmetric induction varied between 0.3 and 49percent and was in some cases improved by the presence of the R* ligand.The influence of substituents on the β-carbon of the α,β-unsaturated esters on the stereochemical course of the reaction is related to their coordination ability.The directing effects of the chiral ester functions are discussed.
