145654-55-3Relevant academic research and scientific papers
Selective Approaches to α- and β-Arylated Vinyl Ethers
Bolm, Carsten,Domzalska-Pieczykolan, Anna,Funes-Ardoiz, Ignacio,Furman, Bart?omiej
supporting information, (2021/11/30)
We developed simple and efficient protocols for palladium-catalyzed regioselective α- and β-arylations of structurally diverse vinyl ethers. Both catalytic methods proceed under relatively mild reactions conditions applying to a broad substrate range including more complex compounds providing arylated glucal or isochromene. Lacking the common requirement of a large reagent excess, the transformations are highly economic and limiting the waste production. Results from computational studies (DFT) provided insight into the key factors determining the pronounced regioselectivities of the investigated reactions.
Synthesis of enol ethers and enamines by Pd-catalyzed tosylhydrazide- promoted cross-coupling reactions
Barluenga, Jose,Escribano, Maria,Moriel, Patricia,Aznar, Fernando,Valdes, Carlos
supporting information; experimental part, p. 13291-13294+13273 (2010/06/15)
"Chemical Equation Presented" α-Substitution is fine: α-Alkoxycarbonyl and α-aminocarbonyl compounds are good substrates for the recently developed tosylhydrazide-promoted Pd-catalyzed cross-coupling of carbonyls with aryl halides. The reac-tion gives ris
Stereoselective Synthesis of Vinyl Ethers by the Reaction of N-(Arylidene(or alkylidene)amino)-2-azetidinones with Ozone
Alcaide, Benito,Perez-Castells, Javier,Polanco, Concepcion,Sierra, Miguel A.
, p. 6012 - 6016 (2007/10/03)
Ozonolysis of N-(arylidene(or alkylidene)amino)-2-azetidinones followed by NaBH4 workup yields enol ethers in good yields with high levels of stereoselectivity.Di- and trisubstituted olefin derivatives are available through this procedure.Chiral 2-azetidinones lead to enol ethers with a chiral moiety without racemization.The reaction is thought to occur through a novel B-type fragmentation of the 2-azetidinone ring.This process is closely related to the well-known N-nitrosoamide to ester rearrangement and the decarboxylation of oxetan-2-ones.
A Novel Fragmentation of the β-Lactam Ring: Stereoselective Entry to Vinyl Ethers by Reaction of N-(Arylidene(or alkylidene)amino-2-azetidinones with Ozone
Alcaide, Benito,Miranda, Miguel,Perez-Castells, Javier,Sierra, Miguel A.
, p. 297 - 298 (2007/10/02)
The title compounds undergo a novel 2-azetidinone ring fragmentation by reaction with ozone followed by NaBH4 workup to stereoselectively yield vinyl ethers via intermediate N-nitroso-β-lactams.
