937-58-6Relevant articles and documents
Palladium-Catalyzed Tandem Hydrocarbonylative Lactamization and Cycloaddition Reaction for the Construction of Bridged Polycyclic Lactams
Xu, Pengcheng,Qian, Bo,Hu, Bin,Huang, Hanmin
supporting information, p. 147 - 151 (2022/01/04)
The intramolecular hydroaminocarbonylation of alkenes is a compelling tool to rapidly access lactam, a privileged motif ubiquitous in natural products, pharmaceuticals, and agrochemicals. However, selective carbonylation to bridged polycyclic lactams with a lactam nitrogen at a bridgehead position is less explored. We herein report a modular palladium-catalyzed approach to perform a tandem hydrocarbonylative lactamization/Diels-Alder cycloaddition reaction with 2-vinyl aryl aldimines, alkenes, and CO, which offers convenient access to furnish the bridged polycyclic lactams in high yields with high selectivities.
Highly Regioselective 5-endo-tet Cyclization of 3,4-Epoxy Amines into 3-Hydroxypyrrolidines Catalyzed by La(OTf)3
Hoshino, Yoshihiko,Iwabuchi, Yoshiharu,Kuriyama, Yuse,Sasano, Yusuke,Uesugi, Shun-ichiro,Yamaichi, Aoto
, p. 1961 - 1965 (2021/01/04)
Highly regioselective intramolecular aminolysis of 3,4-epoxy amines has been achieved. Key features of this reaction are (1) chemoselective activation of epoxides in the presence of unprotected aliphatic amines in the same molecules by a La(OTf)3 catalyst and (2) excellent regioselectivity for anti-Baldwin 5-endo-tet cyclization. This reaction affords 3-hydroxy-2-alkylpyrrolidines stereospecifically in high yields. DFT calculations revealed that the regioselectivity might be attributed to distortion energies of epoxy amine substrates. The use of this reaction was demonstrated by the first enantioselective synthesis of an antispasmodic agent prifinium bromide.
Directed Nickel-Catalyzed Diastereoselective Reductive Difunctionalization of Alkenyl Amines
Zhao, Lei,Meng, Xiao,Zou, Yifeng,Zhao, Junsong,Wang, Lili,Zhang, Lanlan,Wang, Chao
, p. 8516 - 8521 (2021/10/25)
We report herein an intermolecular syn-arylalkylation and alkenylalkylation of alkenyl amines with two different organohalides (iodides and bromides) using Ni(II) catalyst. The cleavable bidentate quinolinamide is utilized after extensive directing group screening to enable olefin difunctionalization with high levels of regio-, chemo-, and diastereocontrol. This general and practical protocol is compatible with α- or β-substituted terminal alkenes and internal alkenes, providing rapid access to branched aliphatic amines bearing two skipped and vicinal stereocenters with high diastereoselectivities that would otherwise be difficult to synthesize.
