314734-23-1Relevant academic research and scientific papers
Intramolecular cascade rearrangements of enynamine derived ketenimines: Access to acyclic and cyclic amidines
Chauhan, Dinesh Pratapsinh,Varma, Sreejith J.,Gudem, Mahesh,Panigrahi, Nihar,Singh, Khushboo,Hazra, Anirban,Talukdar, Pinaki
, p. 4822 - 4830 (2017)
Copper-catalyzed reaction of enynamines with sulfonylazides provides acyclic and cyclic amidines. Nucleophilic addition of the tethered amino group on the in situ generated ketenimine forms a six-membered cyclic zwitterionic intermediate which facilitates
Gold(l)-catalyzed formation of furans by a Claisen type rearrangement of ynenyl allyl ethers
Istrate, Florin M.,Gagosz, Fabien
supporting information; experimental part, p. 878 - 885 (2011/09/20)
A series of ynenyl allyl ethers were rearranged into polysubstituted furans in the presence of a gold(I) catalyst. It is proposed that the transformation involves a Claisen-type rearrangement that allows the efficient creation of quaternary centers under mild experimental conditions.
An unusual access to medium sized cycloalkynes by a new goId(I)-catalysed cycloisomerisation of diynes
Odabachian, Yann,Le Goff, Xavier F.,Gagosz, Fabien
supporting information; scheme or table, p. 8966 - 8970 (2010/04/25)
A study was conducted to demonstrate efficient cycloisomerization of a series of 1,9- and 1,10-diynes into medium sized cycloalkynes by a gold-catalyzed alkyne-alkyne coupling. The reaction was performed using 4 mol% of gold complex in CD2Cl2 at room temperature and was monitored by using 1H NMR spectroscopy. The reaction of analogous diyne substrate was more rapid and a complete conversion was observed after 40 hours at room temperature. The cycloalkyne was isolated as a solid in 95% yield from which single crystals suitable for X-ray crystal structure determination was obtained. A rapid screening of catalysts and experimental conditions was undertaken to optimize the formation of cycloalkyne. A mechanistic proposal was also introduced for the cycloisomerization of diynes into cycloalkynes on the basis of the experimental observations.
Synthesis of functionalized furans via gold(I)-catalyzed Claisen-type rearrangement
Istrate, Florin M.,Gagosz, Fabien L.
, p. 730 - 733 (2008/09/17)
(Chemical Equation Presented) Gold(I)-catalyzed cyclization of pentenynyl allyl ethers allows the rapid construction of functionalized furans. The concerted oxy-Claisen-type mechanism induces a complete selectivity of the process and allows the easy forma
8-Phenyl-10,10a-dihydropyrido[1,2-a]azepines by 1,7-electrocyclization of conjugated pyridinium ylides - rationalization of the periselectivity
Marx, Karsten,Eberbach, Wolfgang
, p. 2063 - 2068 (2007/10/03)
Base treatment of the pyridinium bromides 11a-e gives rise to the formation of the dihydropyridoazepines 14a-e as the only monomolecular products. The reaction takes place by initial deprotonation to the ylides 12, which undergo 8π-electrocyclization affording the seven-membered-ring systems; no products of a dipolar 6π-cyclization were detected. On the basis of quantum mechanical calculations a rationalization of the periselectivity of the electrocyclization process is given.
