493009-89-5Relevant academic research and scientific papers
Palladium(II)-catalyzed intramolecular hydroamination of 1,3-dienes to give homoallylic amines
Pierson, Justin M.,Ingalls, Erica L.,Vo, Richard D.,Michael, Forrest E.
supporting information, p. 13311 - 13313 (2014/01/06)
A pincer for high selectivity: A mild palladium-catalyzed hydroamination of protected amino-1,3-dienes is possible. This highly regioselective reaction employs a tridentate PNP pincer ligand and leads to cyclic and homoallylic protected amines in high yields. Substrates with a wide array of amine protecting groups and diene substitution patterns were cyclized to form five- and six-membered heterocycles. PG=protecting group.
Electrochemical deallylation of α-allyl cyclic amines and synthesis of optically active quaternary cyclic amino acids
Kirira, Peter G.,Kuriyama, Masami,Onomura, Osamu
experimental part, p. 3970 - 3982 (2010/07/04)
Electrochemical oxidation of α-allylated and α-betizylated N-acylated cyclic amines by using a graphite anode easily affords the corresponding α-methoxylated products with up to 76% yield. Ease of oxidation was affected by the type of electrode, the size
High regioselectivity in electrochemical α-methoxylation of N-protected cyclic amines
Libendi, Samuel S.,Demizu, Yosuke,Matsumura, Yoshihiro,Onomura, Osamu
, p. 3935 - 3942 (2008/09/20)
N-Protecting groups of α-substituted cyclic amines strongly affected the regioselectivity in electrochemical methoxylation of these compounds. Namely, N-acyl derivatives were transformed into α′-methoxylated compounds, while N-cyano derivatives changed into α-methoxylated derivatives. Furthermore, Lewis acid catalyzed nucleophilic substitution of the α-methoxylated compounds protected with cyano group afforded α,α-disubstituted cyclic amines.
Solid-phase synthesis of piperidines by N-acyliminium ion chemistry
Veerman, Johan J. N.,Klein, Jasper,Aben, Rene W. M.,Scheeren, Hans W.,Kruse, Chris G.,Van Maarseveen, Jan H.,Rutjes, Floris P. J. T.,Hiemstra, Henk
, p. 3133 - 3139 (2007/10/03)
An efficient solid-phase procedure for the synthesis of a number of 2-substituted piperidines is reported. Starting from solid-supported carbamate -tethered δ-amino acetals, 2- benzotriazolyl- substituted (Bt-substituted) piperidines were obtained by acid-induced ring-closure followed by trapping of the transient N-acyliminium ions with benzotriazole. These 2-Bt-substituted piperidines were then used as precursors for the successful introduction of several C-nucleophiles by N-acyliminium ion chemistry. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
