190002-16-5Relevant academic research and scientific papers
Palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination: Access to functionalized naphthalenes
Yu, Bangkui,Yu, Houjian,Huang, Hanmin
supporting information, p. 8962 - 8966 (2020/11/13)
A palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination of enyne-tethered allylic alcohols with aminals is described. Under the reaction conditions, the cationic vinyl allylpalladium species undergoes selective migratory insertion of alkenes rather than reductive elimination with nucleophiles. This strategy provides an efficient and unique approach to the construction of functionalized naphthalenes, which are important building blocks in synthetic organic chemistry. Mechanistic studies have revealed that the selective sequential migratory insertion of enyne and alkene is crucial for the cyclization.
Rapid Access to Oxabicyclo[2.2.2]octane Skeleton through Cu(I)-Catalyzed Generation and Trapping of Vinyl-o-quinodimethanes (Vinyl-o-QDMs)?
Luo, Hejiang,He, Chuan,Jiang, Huanfeng,Zhu, Shifa
supporting information, p. 1052 - 1056 (2020/07/04)
A Cu(I)-catalyzed three-component reaction of terminal enynals/enynones, diazo compounds, and alkenes has been developed. With this method, a series of oxabicyclo[2.2.2]octanes were effectively synthesized in high yields under mild reaction conditions. This transformation is proposed to proceed through trapping of the cyclic vinyl-o-quinodimethanes (vinyl-o-QDMs) species, which were generated from terminal enynals/enynones and diazo compounds by alkenes. The obvious advantages of wide substrate scopes, mild reaction conditions, and high seteroselectivity and atom efficiency make this reaction highly appealing for construction of highly rigid [2.2.2]octane skeleton.
Stereoselective Synthesis of Oxabicyclo[2.2.1]heptenes via a Tandem Dirhodium(II)-Catalyzed Triazole Denitrogenation and [3 + 2] Cycloaddition
Yuan, Hao,Gong, Jianxian,Yang, Zhen
supporting information, p. 5500 - 5503 (2016/11/17)
A novel synthetic strategy for the diastereoselective synthesis of structurally diverse oxabicyclo[2.2.1]heptenes has been developed, featuring a tandem reaction combining a Rh-catalyzed triazole denitrogenation and a novel type of [3 + 2] cycloaddition reaction. This tandem reaction was thought to proceed via a five-membered oxonium ylide intermediate, which was formed by the intramolecular nucleophilic attack of the carbonyl group on the α-imino metallocarbene followed by an inter- or intramolecular [3 + 2] dipolar cycloaddition with a range of alkynes and alkenes.
Tandem Enyne Metathesis-Diels-Alder Reaction for Construction of Natural Product Frameworks
Rosillo, Marta,Dominguez, Gema,Casarrubios, Luis,Amador, Ulises,Perez-Castells, Javier
, p. 2084 - 2093 (2007/10/03)
Enynes connected through aromatic rings are used as substrates for metathesis reactions. The reactivity of three ruthenium carbene complexes is compared. The resulting 1,3-dienes are suitable precursors of polycyclic structures via a Diels-Alder process.
Diastereoselective Pauson-Khand reactions on aromatic substrates
Blanco-Urgoiti, Jaime,Casarrubios, Luis,Domínguez, Gema,Pérez-Castells, Javier
, p. 3315 - 3317 (2007/10/03)
The synthesis of several natural products' frameworks is carried out by means of a diastereoselective intramolecular Pauson-Khand reaction promoted by molecular sieves. Diastereoselectivity is achieved only if a coordinating group is present at a convenie
