3020-28-8Relevant articles and documents
Electron-Catalyzed Aminocarbonylation: Synthesis of α,β-Unsaturated Amides from Alkenyl Iodides, CO, and Amines
Picard, Baptiste,Fukuyama, Takahide,Bando, Takanobu,Hyodo, Mamoru,Ryu, Ilhyong
supporting information, p. 9505 - 9509 (2021/12/09)
Aminocarbonylation of alkenyl iodides with CO and amines proceeded under heating to produce α,β-unsaturated amides in good yields (23 examples, 71% average yield). This catalyst-free method exhibited good functional-group tolerance, and open a straightforward access to functionalized acrylamides, as illustrated by the synthesis of Ilepcimide. A hybrid radical/ionic mechanism involving chain electron transfer is proposed for this transformation.
Protecting group free, stereocontrolled synthesis of β-halo-enamides
Pasqua, Adele E.,Crawford, James J.,Long, De-Liang,Marquez, Rodolfo
experimental part, p. 2149 - 2158 (2012/05/20)
Enamides, dienamides, and enynamides are important building blocks in synthetic, biological, and medicinal chemistry as well as materials science. Despite the extensive breath of their potential utility in synthetic chemistry, there is a lack of simple, high-yielding methods to deliver them efficiently and as single isomers. In this paper, we present a novel, protecting group free, efficient, and stereoselective approach to the generation of β-halo-enamides. The methodology presented provides a robust synthetic platform from which E- or Z-enamides can be generated in good yields and with complete stereocontrol.
Total synthesis of iso- and bongkrekic acids: Natural antibiotics displaying potent antiapoptotic properties
Francais, Antoine,Leyva-Perez, Antonio,Etxebarria-Jardi, Gorka,Pena, Javier,Ley, Steven V.
supporting information; experimental part, p. 329 - 343 (2011/03/21)
For over five decades, owing to their antiapoptotic activities, bongkrekic and isobongkrekic acids have generated interest from the scientific community. Here, we disclose full details of our investigation into the synthesis of isobongkrekic acid, which culminated in its first preparation and features various palladium-catalysed cross-couplings and Takai olefination reactions. Access to bongkrekic acid is also reported by this route. These syntheses involve the preparation and use of new general building blocks which could find wider applications. Iso-bong: A versatile first synthesis of isobongkrekic acid (IBA) has been developed. Key steps include three different palladium cross-couplings and an asymmetric homopropargylation. In-depth synthetic studies reveal the challenges faced in generating the right geometry of each diene.
