141089-33-0Relevant academic research and scientific papers
Preparation of (E)-1,3-Enyne Derivatives through Palladium Catalyzed Hydroalkynylation of Allenes
Liu, Zhi-Kai,Yang, Ying,Zhan, Zhuang-Ping
supporting information, p. 1589 - 1597 (2022/01/20)
A general and efficient palladium catalyzed hydroalkynylation of allenes was developed to produce synthetically versatile (E)-1,3-enyne derivatives with high regio- and stereoselectivity. This catalytic system proceeded under mild conditions and was compatible with a broad range of substrates, especially for allenes without electron-bias groups. This work further broadens the synthetic potential of these scaffolds in organic synthesis and medicinal chemistry.
Remote Cooperative Group Strategy Enables Ligands for Accelerative Asymmetric Gold Catalysis
Wang, Zhixun,Nicolini, Corrado,Hervieu, Cedric,Wong, Yuk-Fai,Zanoni, Giuseppe,Zhang, Liming
, p. 16064 - 16067 (2017/11/22)
An accelerative asymmetric gold catalysis is achieved for the first time via chiral ligand metal cooperation. An asymmetrically positioned remote amide group in the designed chiral binaphthyl-based ligand plays the essential role of a general base catalyst and selectively accelerates the cyclizations of 4-allen-1-ols into one prochiral allene face. The reactions are mostly highly enantioselective with achiral substrates, and due to the accelerated nature of the catalysis catalyst loadings as low as 100 ppm are allowed. With a pre-existing chiral center at any of the backbone sp3-carbons, the reaction remained highly efficient and most importantly maintained excellent allene facial selectivities regardless of the substrate stereochemistry. By using different combinations of ligand and substrate enantiomers, it is now possible to access all four stereoisomers of versatile 2-vinyltetrahydrofurans with exceedingly high selectivity. The underpinning design of this chemistry reveals a novel and conceptually distinctive strategy to tackle challenging asymmetric gold catalysis, which to date has relied on decelerative asymmetric steric hindrance approaches.
A new five-membered ring forming process based on palladium(0)-catalyzed arylative cyclization of allenyl enones
Tsukamoto, Hirokazu,Kondo, Yoshinori
supporting information; experimental part, p. 2633 - 2636 (2009/05/30)
(Chemical Equation Presented) A palladium(0)/monophosphine catalyst promotes a novel arylative cyclization reaction of C1-, C2-, and C3-tethered allenyl enones with arylboronic acids to produce five-membered ring containing products. The regioselectivity of the process, associated with aryl group introduction into the allene moiety, depends on the length of the tether. This finding suggests that the cyclization reaction does not proceed through a carbopalladation pathway but rather via a route involving palladacycle-forming or anti-Wacker -type oxidative addition to the Pd0 catalyst.
