55629-97-5Relevant academic research and scientific papers
Stereo- and Regioselective [3+3] Annulation Reaction Catalyzed by Ytterbium: Synthesis of Bicyclic 1,4-Dihydropyridines
del Corte, Xabier,López-Francés, Adrián,de Marigorta, Edorta Martínez,Palacios, Francisco,Vicario, Javier
, p. 4761 - 4769 (2021/08/23)
An ytterbium catalyzed formal [3+3] cycloaddition of cyclic enamines and α,β-unsaturated ketones catalyzed is reported. The reaction proceeds with a ‘head to tail’ regioselectivity through a conjugate addition of the enamine moiety followed by an amine-carbonyl condensation. In addition the use of chiral enamines provided a high degree of stereoselectivity, driven by a possible balance between steric and π-stacking effects. The resulting bicyclic 1,4-dihydropyridines were evaluated as antiproliferative agents against A549 (carcinomic human alveolar basal epithelial cell) and SKOV3 (human ovarian carcinoma) human tumor cell lines. Good toxicities were found for some of the compounds against A549 and SKOV3 cell lines, with best IC50 values of 0.89 μM for A549 and 6.69 μM for SKOV3, and a very good selectivity was observed towards MRC5 (non-malignant) cell lines. (Figure presented.).
Diversity-Oriented Synthesis of Spirocyclohexene Indane-1,3-diones and Coumarin-Fused Cyclopentanes via an Organobase-Controlled Cascade Reaction
Wang, Min,Tseng, Ping-Yao,Chi, Woei-Jye,Suresh, Sundaram,Edukondalu, Athukuri,Chen, Yi-Ru,Lin, Wenwei
, p. 3407 - 3415 (2020/07/16)
An organobase-controlled, divergent cascade reaction to construct spirocyclohexene indane-1,3-diones and coumarin-fused cyclopentanes is reported. The cascade reaction is triggered by the 1,6-addition of 3-homoacylcoumarins to the indanedione-derived acce
Direct Synthesis of β,γ-Unsaturated α-Keto Esters from Aldehydes and Pyruvates
Mansaray, John Kamanda,Sun, Jiarui,Huang, Shisheng,Yao, Weijun
supporting information, p. 809 - 813 (2019/04/25)
Herein, we describe two practical methods to synthesize β,γ-unsaturated α-keto esters directly from aldehydes and pyruvates promoted by BF 3 ?Et 2 O in the presence of Ac 2 O or by Ti(OEt) 4 under mild condition
A mild method for indium(III)-catalyzed 1,4-hydrosilylation of α,β-enone esters with triethylsilane and trifluoroacetic acid
Xing, Ping,Zang, Wei,Huang, Zuo-Gang,Zhan, Yue-Xiong,Zhu, Chuan-Jun,Jiang, Biao
, p. 2269 - 2273 (2012/10/30)
A chemo- and stereoselective 1,4-hydrosilylation of α,β-enone esters was developed using triethylsilane and trifluoroacetic acid under indium chloride catalysis. Georg Thieme Verlag Stuttgart ? New York.
Enantioselective copper-catalyzed conjugate addition of trimethylaluminium to β,γ-unsaturated α-ketoesters
Gremaud, Ludovic,Alexakis, Alexandre
, p. 794 - 797 (2012/03/09)
Not a cop out: The copper-catalyzed asymmetric conjugate addition of organometallic reagents to Michael acceptors is an important methodology for forming a C-C bond in an enantioselective manner. Such an addition of Me 3Al to β,γ-unsaturated α-
Organocatalytic Functionalization of carboxylic acids: Isothiourea- catalyzed asymmetric intra- and intermolecular Michael addition-lactonizations
Belmessieri, Dorine,Morrill, Louis C.,Simal, Carmen,Slawin, Alexandra M. Z.,Smith, Andrew D.
, p. 2714 - 2720 (2011/04/23)
Tetramisole promotes the catalytic asymmetric intramolecular Michael addition-lactonization of a variety of enone acids, giving carbo- and heterocyclic products with high diastereo- and enantiocontrol (up to 99:1 dr, up to 99% ee) that are readily derivatized to afford functionalized indene and dihydrobenzofuran carboxylates. Chiral isothioureas also promote the catalytic asymmetric intermolecular Michael addition-lactonization of arylacetic acids and α-keto-β,γ-unsaturated esters, giving anti-dihydropyranones with high diastereo- and enantiocontrol (up to 98:2 dr, up to 99% ee).
An efficient synthesis of achiral and chiral cyclic dehydro-α-amino acid derivatives through nucleophilic addition of amines to β,γ- unsaturated α-keto esters
Palacios, Francisco,Vicario, Javier,Aparicio, Domitila
, p. 2843 - 2850 (2007/10/03)
A very simple and efficient synthesis of 3-amino-1,5-dihydro-2H-pyrrol-2- ones is reported. These cyclic dehydro-amino acid derivatives with a stereogenic center at the 5-position were obtained by the addition of two equivalents of amine to β,γ-unsaturate
