1095320-64-1Relevant academic research and scientific papers
Unexpected Direct Synthesis of N-Vinyl Amides through Vinyl Azide–Enolate [3+2] Cycloaddition
Choi, Hans,Shirley, Harry J.,Hume, Paul A.,Brimble, Margaret A.,Furkert, Daniel P.
, p. 7420 - 7424 (2017)
The unexpected synthesis of industrially important N-vinyl amides directly from aldehydes and α,β-unsaturated N-vinyl amides from esters is reported. This reaction probably proceeds through an initial [3+2] azide–enolate cycloaddition involving a vinyl azide generated in situ. A survey of the reaction scope and preliminary mechanistic findings supported by quantum computational analysis are reported, with implications for the future development of atom-efficient amide synthesis. Intriguingly, this study suggests that (cautious) reevaluation of azidoethene as a synthetic reagent may be warranted.
Ruthenium-catalyzed addition of primary amides to alkynes: A stereoselective synthesis of secondary enamides
Goossen, Lukas J.,Blanchot, Mathieu,Salih, Kifah S. M.,Goossen, Kaethe
experimental part, p. 2283 - 2288 (2009/12/27)
The anti-Markovnikov addition of primary amides to terminal alkynes under the formation of Z-configured secondary enamides is efficiently promoted by a catalyst system generated in situ from bis(2-methallyl)(cycloocta-1,5-diene) ruthenium(II), 1,4-bis(dic
Synthesis of secondary enamides by ruthenium-catalyzed selective addition of amides to terminal alkynes
Goossen, Lukas J.,Salih, Kifah S. M.,Blanchot, Mathieu
supporting information; experimental part, p. 8492 - 8495 (2009/05/11)
(Chemical Equation Presented) Enamides made easy: A catalyst system generated in situ using bis(2-methallyl)-(cycloocta-1,5-diene)ruthenium(II), 1,4-bis(dicyclohexylphosphino)butane, and ytterbium triflate efficiently catalyzes the addition of primary amides to terminal alkynes, selectively forming the Z-anti-Markovnikov enamides. The E isomers are also accessible by combining the hydroamidation with an in situ double-bond isomerization reaction.
