849092-82-6Relevant academic research and scientific papers
Ag(i)/PPh3-catalyzed diastereoselective syntheses of spiro[indole-3,4′-piperidine] derivatives via cycloisomerizations of tryptamine-ynamides
Chen, Yanyu,Cheng, Maosheng,Lin, Bin,Liu, Yongxiang,Sun, Shitao,Wang, Zhaobo,Yang, Lu,Zhang, Di,Zhang, Junpeng,Zhao, Wutong
, p. 3051 - 3054 (2022/03/16)
A Ag(i)/PPh3-catalyzed chelation-controlled cycloisomerization of tryptamine-ynamide was developed to access the spiro[indole-3,4′-piperidine] scaffold in a racemic and diastereoselective manner. The diastereoselective products were achieved by a chiron approach. Density functional theory (DFT) calculations indicated that strong non-covalent effects between the substrate and catalyst/ligand complex stabilized the spiroindoleninium intermediate via cation-π-π interactions.
Copper(II)-catalyzed amidations of alkynyl bromides as a general synthesis of ynamides and Z-enamides. An intramolecular amidation for the synthesis of macrocydic ynamides
Zhang, Xuejun,Zhang, Yanshi,Huang, Jian,Hsung, Richard P.,Kurtz, Kimberly C. M.,Oppenheimer, Jossian,Petersen, Matthew E.,Sagamanova, Irina K.,Shen, Lichun,Tracey, Michael R.
, p. 4170 - 4177 (2007/10/03)
A general and efficient method for the coupling of a wide range of amides with alkynyl bromides is described here. This novel amidation reaction involves a catalytic protocol using copper(II) sulfate-pentahydrate and 1,10-phenanthroline to direct the sp-C-N bond formation, leading to a structurally diverse array of ynamides including macrocyclic ynamides via an intramolecular amidation. Given the surging interest in ynamide chemistry, this atom economical synthesis of ynamides should invoke further attention from the synthetic organic community.
Bronsted acid-catalyzed highly stereoselective arene-ynamide cyclizations. A novel keteniminium Pictet-Spengler cyclization in total syntheses of (±)-desbromoarborescidines A and C
Zhang, Yanshi,Hsung, Richard P.,Zhang, Xuejun,Huang, Jian,Slafer, Brian W.,Davis, Allison
, p. 1047 - 1050 (2007/10/03)
(Chemical Equation Presented) A Bronsted acid-catalyzed highly stereoselective arene-ynamide cyclization is described. These reactions constitute a keteniminium variant of Pictet-Spengler cyclizations, leading to efficient synthesis of nitrogen heterocycl
