55629-97-5Relevant articles and documents
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.).
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
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-