107969-78-8Relevant articles and documents
Interaction of hydroxylamine with esters of 2-oxobutenoic acids. Synthesis of 1-hydroxy-3-hydroximino-2-pyrrolidinones
Katkevics,Korchagova,Ivanova,Slavinska,Lukevics
, p. 734 - 741 (2004)
New 3-hydroximino-1-hydroxy-2-pyrrolidinones have been synthesized by the interaction of NH2OH and NH2OBn with the methyl esters of 2-oxo-3-butenoic acid derivatives. Some intermediate compounds have been isolated and identified and
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.).
Asymmetric Catalytic Formal 1,4-Allylation of β,γ-Unsaturated α-Ketoesters: Allylboration/Oxy-Cope Rearrangement
Tang, Qiong,Fu, Kai,Ruan, Peiran,Dong, Shunxi,Su, Zhishan,Liu, Xiaohua,Feng, Xiaoming
, p. 11846 - 11851 (2019/07/19)
A highly enantioselective formal conjugate allyl addition of allylboronic acids to β,γ-unsaturated α-ketoesters has been realized by employing a chiral NiII/N,N′-dioxide complex as the catalyst. This transformation proceeds by an allylboration/oxy-Cope rearrangement sequence, providing a facile and rapid route to γ-allyl-α-ketoesters with moderate to good yields (65–92 %) and excellent ee values (90–99 % ee). The isolation of 1,2-allylboration products provided insight into the mechanism of the subsequent oxy-Cope rearrangement reaction: substrate-induced chiral transfer and a chiral Lewis acid accelerated process. Based on the experimental investigations and DFT calculations, a rare boatlike transition-state model is proposed as the origin of high chirality transfer during the oxy-Cope rearrangement.