189809-15-2Relevant academic research and scientific papers
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.
Stereoselective synthesis of enamides by a Peterson reaction manifold
Fuerstner, Alois,Brehm, Christof,Cancho-Grande, Yolanda
, p. 3955 - 3957 (2007/10/03)
equation presented Vinylsilanes are converted into enamides by a sequence comprising epoxidation, nucleophilic ring opening of the resulting epoxysilanes with NaN3, and reduction of the azide, followed by a "one-pot" N-acylation/Peterson elimin
α-Nitrogenated organolithium compounds from N-(tosylmethyl)amides
Alonso, Diego A.,Alonso, Emma,Nájera, Carmen,Yus, Miguel
, p. 491 - 492 (2007/10/03)
Deprotonation of α-amido sulfones 7 with BunLi at -90°C followed by reaction with electrophiles leads, depending on the substitution on the amidic nitrogen to enamides 10 (secondary amides 7a,b) or functionalised α-amido sulfones 12 (tertiary amides 7c,d). Naphthalene-catalysed lithiation of tertiary α-amido sulfones 7c,d in the presence of electrophiles (Barbier conditions) at -78°C affords functionalised amides 13.
