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A bis(imidazolidine)pyridine (PyBidine)-Cu(OTf)2 complex catalyzing the endo-selective [3+2] cycloaddition of nitroalkenes with imino esters was applied to the reaction of methyleneindolinones with imino esters to afford spiro[pyrrolidin-3,3'-oxindole]s in up to 98 % ee. X-ray crystallographic analysis of the PyBidine-Cu(OTf)2 complex and DFT calculations… (More)
The catalytic asymmetric Friedel-Crafts/protonation of indoles and pyrroles with α-substituted nitroalkenes to give the corresponding adducts in a highly anti-selective manner was achieved by an imidazoline-aminophenol (L2)-Cu complex. The anti-adducts could be successfully transformed to biochemically important α-substituted β-heteroarylalkylamines.
Indoles are composed of a common core structure, the indole ring, and are widely used as pharmaceuticals and their precursors. In this study, a newly composed relatively small indole compound, AWT-489 was examined to find a novel specific antagonist for DP receptors; the cognate receptors for prostaglandin D2 (PGD2), to prevent colon cancer malignancy. Here… (More)
The structure of a nickel complex of imidazoline-aminophenol (IAP) prepared from IAP with Ni(OAc)2 was elucidated as cis-bis(imidazolineaminophenoxide) [Ni(IAP)2]. The [Ni(IAP)2] complex smoothly promoted catalytic asymmetric 1,4-addition of 3'-indolyl-3-oxindole to nitroethylene to provide chiral mixed 3,3'-bisindoles with high enantioselectivities.… (More)
A chiral bis(imidazolidine)pyridine (PyBidine)-Ni(OTf)2 complex smoothly catalyzed an asymmetric Friedel-Crafts reaction of 2-vinylindoles with nitroalkenes to give chiral indoles in a highly enantioselective manner while maintaining the 2-vinyl functionality. The chiral 2-vinylindoles offer unique chiral scaffolds for diverse transformations.
The stereochemical divergent synthesis of indolyl-pyrrolidines was accomplished using an imidazoline-aminophenol (IAP)-Ni(OAc)2 complex and a bis(imidazolidine)pyridine (PyBidine)-Cu(OTf)2 complex. The former catalyzed exo'-selective asymmetric [3 + 2] cyclization of iminoesters with indolyl nitroalkenes, and the latter catalyzed the reaction in an… (More)
TOP class: The first efficient catalytic asymmetric coupling reaction of indoles with isatin-derived nitroalkenes was accomplished by using a complex consisting of a chiral imidazoline aminophenol ligand (1; see scheme) and Cu(OTf)(2). Biological activity of the newly formed chiral 3,3'-bisindoles was also confirmed in a Wnt signaling inhibitory assay.