957770-68-2Relevant academic research and scientific papers
Combined Computational and Experimental Studies on the Asymmetric Michael Addition of α-Aminomaleimides to β-Nitrostyrenes Using an Organocatalyst Derived from Cinchona Alkaloid
Sakai, Naoki,Kawashima, Kyohei,Kajitani, Masashi,Mori, Seiji,Oriyama, Takeshi
, p. 5714 - 5718 (2021)
Maleimides are often used as electrophiles in conventional reactions; however, their application as nucleophiles is limited to only a few reactions, and reactions utilizing α-aminomaleimides as asymmetric Michael donors have not been reported to date. Thus, in this work, asymmetric Michael addition of α-aminomaleimides as Michael donors to β-nitrostyrenes was conducted for the first time using an organocatalyst derived from a Cinchona alkaloid. Density functional theory investigations were crucial to improve the enantioselectivity of the adduct.
Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolinesviaSNAr
Cardenas, Mariel M.,Saputra, Mirza A.,Gordon, Deane A.,Sanchez, Andrea N.,Yamamoto, Nobuyuki,Gustafson, Jeffrey L.
supporting information, p. 10087 - 10090 (2021/10/06)
Herein we report the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolinesviathe nucleophilic aromatic substitution (SNAr) of thiophenols into 3-aryl-2-fluoroquinolines mediated by catalytic amounts of Cinchona alkaloid-derived ureas. These reactions displayed a spectrum of dynamic kinetic resolution (DKR) and kinetic resolution (KR) characters depending upon the stereochemical stability of the starting material. Low barrier substrates proceededviaDKR while higher barrier substrates proceededviaKR. On the other hand, substrates with intermediate stabilities displayed hallmarks of both DKR and KR. Finally, we also show that we can functionalize the atropisomerically enriched quinolines into pharmaceutically privileged scaffolds with minimal observed racemization.
Enantioselective Bromolactonization of Deactivated Olefinic Acids
Jiang, Xiaojian,Liu, Shenghui,Yang, Si,Jing, Mei,Xu, Lipeng,Yu, Pei,Wang, Yuqiang,Yeung, Ying-Yeung
supporting information, p. 3259 - 3262 (2018/06/11)
A novel enantioselective bromolactonization of α,β-unsaturated ketones using bifunctional amino-urea catalysts has been developed. The scope of the reaction is evidenced by 23 examples of halolactones bearing various functionalities with up to 99% yield a
