72196-18-0Relevant academic research and scientific papers
Synthesis of 6-Substituted Piperidin-3-ones via Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles with Electron-Rich Aromatic Nucleophiles
Li, Yang,Zhang, Ran,Ali, Arshad,Zhang, Jing,Bi, Xihe,Fu, Junkai
supporting information, p. 3087 - 3090 (2017/06/23)
A highly diastereoselective rhodium(II)-catalyzed transannulation of aldehyde-tethered N-sulfonyl triazoles with electron-rich aromatic nucleophiles is reported for the first time to afford functionalized 6-substituted piperidin-3-ones. The reaction has a broad substrate scope including both aliphatic and aromatic N-sulfonyl-1,2,3-triazoles together with various aromatic nucleophiles. The addition of a catalytic amount of Lewis acid has proven to be crucial for the yield improvement. By employing this methodology, hardly accessible piperidin-3-ones bearing quaternary carbons could be obtained.
Gold(I)-catalysed intramolecular hydroamination of α-quaternary alkynes: Synthetic studies towards spiroimine marine toxins
Zhang, Yanchuan C.,Furkert, Daniel P.,Guéret, Stéphanie M.,Lombard, Fanny,Brimble, Margaret A.
scheme or table, p. 4896 - 4898 (2011/10/05)
Cyclic spiroimines form an essential component of the bioactive pharmacophore in a number of potent fast-acting marine biotoxins, including the pinnatoxins, gymnodimine and the spirolides. These present a significant challenge for the total synthesis of this class of natural products. A novel approach to these cyclic spiroimines based on metal-catalysed hydroamination of spiroaminoalkyne precursors is reported herein. Au(PPh3)SbF 6 was found to effect the formation of bench-stable 5,6- and 6,6-spiroimine systems in high yields, although the 7,6-analogue remained elusive. To the best of our knowledge these are the first reported examples of α-quaternary cyclic imines formed via alkyne hydroamination.
