419554-93-1Relevant articles and documents
Aza-heterocycles via copper-catalyzed, remote C–H desaturation of amines
Dare, Ross M.,Nagib, David A.,Paneque, Alyson N.,Stateman, Leah M.
supporting information, p. 210 - 224 (2022/01/19)
A majority of medicines contain a nitrogen atom within a five- or six-membered ring. To rapidly access both such aza-heterocycles, we sought to develop a remote C–H desaturation of amines. Inspired by the Hofmann-L?ffler-Freytag (HLF) synthesis of five-me
Synthetic efforts toward the Lycopodium alkaloids inspires a hydrogen iodide mediated method for the hydroamination and hydroetherification of olefins
Leger, Paul R.,Murphy, Rebecca A.,Pushkarskaya, Eugenia,Sarpong, Richmond
supporting information, p. 4377 - 4383 (2015/03/14)
Progress toward the total syntheses of a diverse set of fawcettimine-type Lycopodium alkaloids via a "Heathcock-type" 6-5-9 tricycle is disclosed. This route features an intermolecular Diels-Alder cycloaddition to rapidly furnish the 6-5-fused bicycle and a highly chemoselective directed hydrogenation to build the azonane fragment. While conducting these synthetic studies, trimethylsilyl iodide was found to effect a hydroamination reaction to furnish the tetracyclic core of serratine and related natural products. This observation has been expanded into a general method for the room temperature hydroamination of unactivated olefins with tosylamides utilizing catalytic "anhydrous" HI (generated in situ from trimethylsilyl iodide and water). The presence of the iodide anion is critical to the success of this Bronsted acid catalyzed protocol, possibly due to its function as a weakly coordinating anion. These conditions also effect the analogous hydroetherification reaction of alcohols with unactivated olefins.
Electrophilic cyclization of N-alkenylamides using?a chloramine-T/I2 system
Morino, Yoshinobu,Hidaka, Ikumasa,Oderaotoshi, Yoji,Komatsu, Mitsuo,Minakata, Satoshi
, p. 12247 - 12251 (2007/10/03)
A new protocol for the cyclization of N-alkenylamides using chloramine-T and iodine is described. When N-alkenylsulfonamides are treated with chloramine-T and iodine, three- to six-membered N-heterocycles are obtained with complete stereoselectivity. The method is compatible with the cyclization of the allylbenzamide or allylbenzthioamide to afford an oxazoline or thiazoline derivative, respectively. Mechanistic studies indicate that the chloramine-T/I2 system functions as an effective iodonium species.