1356494-18-2Relevant academic research and scientific papers
Palladium-Catalyzed γ,γ′-Diarylation of Free Alkenyl Amines
Fu, Yu,Grant, Aaron J.,Landge, Vinod G.,Payton, John L.,Rabon, Allison M.,Young, Michael C.
, p. 10352 - 10360 (2021/07/26)
The direct difunctionalization of alkenes is an effective way to construct multiple C-C bonds in one-pot using a single functional group. The regioselective dicarbofunctionalization of alkenes is therefore an important area of research to rapidly obtain complex organic molecules. Herein, we report a palladium-catalyzed γ,γ′-diarylation of free alkenyl amines through interrupted chain walking for the synthesis of Z-selective alkenyl amines. Notably, while 1,3-dicarbofunctionalization of allyl groups is well precedented, the present disclosure allows 1,3-dicarbofunctionalization of highly substituted allylamines to give highly Z-selective trisubsubstituted olefin products. This cascade reaction operates via an unprotected amine-directed Mizoroki-Heck (MH) pathway featuring a β-hydride elimination to selectively chain walk to furnish a new terminal olefin which then generates the cis-selective alkenyl amines around the sterically crowded allyl moiety. This operationally simple protocol is applicable to a variety of cyclic, branched, and linear secondary and tertiary alkenylamines, and has a broad substrate scope with regard to the arene coupling partner as well. Mechanistic studies have been performed to help elucidate the mechanism, including the presence of a likely unproductive side C-H activation pathway.
Asymmetric hydrogenation of protected allylic amines
Steinhuebel, Dietrich P.,Krska, Shane W.,Alorati, Anthony,Baxter, Jenny M.,Belyk, Kevin,Bishop, Brian,Palucki, Michael,Sun, Yongkui,Davies, Ian W.
supporting information; experimental part, p. 4201 - 4203 (2010/11/19)
A general method for the enantioselective hydrogenation of protected allylic amine derivatives is described. This procedure relies on the generation of a cationic ruthenium complex with the axially chiral ligand (-)-TMBTP. The utility is highlighted by th
