70882-08-5Relevant academic research and scientific papers
A Rare Alder-ene Cycloisomerization of 1,6-Allenynes
Joyce, Liam M.,Drew, Melanie A.,Tague, Andrew J.,Thaima, Thanaphat,Gouranourimi, Ali,Ariafard, Alireza,Pyne, Stephen G.,Hyland, Christopher J. T.
, (2022/02/07)
Thermally induced cycloisomerization reactions of 1,6-allenynes gives α-methylene-γ-lactams via intramolecular Alder-ene reactions. The mechanism is supported by computational and deuterium labelling studies. This thermal, non-radical method enables the d
Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives
Jovanovic, Milos,Petkovic, Milos,Jovanovic, Predrag,Simic, Milena,Tasic, Gordana,Eric, Slavica,Savic, Vladimir
, p. 295 - 305 (2019/12/24)
Annulations of allene-substituted proline derivatives promoted by transition metals have been investigated as a general way to access bicyclic structures with a bridgehead nitrogen. Two processes, Pd- and Ag-catalysed cyclisations, have been employed comp
Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters
Casavant, Barbara J.,Khoder, Zainab M.,Berhane, Ilyas A.,Chemler, Sherry R.
supporting information, p. 5958 - 5961 (2016/01/09)
A unique method to affect intramolecular aminooxygenation and dioxygenation of allenols and allenylsulfonamides is described. These operationally simple reactions occur under neutral or basic conditions where copper(II) carboxylates serve as reaction promoter, oxidant, and carboxylate source. Moderate to high yields of heterocycle-functionalized vinyl carboxylate esters are formed with moderate to high levels of diastereoselectivity. Such vinyl carboxylate esters could serve as precursors to α-amino and α-oxy ketones and derivatives thereof.
Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts
Yamashita, Kyohei,Hase, Shun,Kayaki, Yoshihito,Ikariya, Takao
, p. 2334 - 2337 (2015/05/27)
Silver(I) carboxylate complexes promote the carboxylative cyclization of allenylmethylamines to afford 5-alkenyl-1,3-oxazolidin-2-ones in 2-propanol. The use of an N-heterocyclic carbene ligand (IPr) under pressurized CO2 is effective in suppre
Pd-catalyzed asymmetric synthesis of N-allenyl amides and their Au-catalyzed cycloisomerizative hydroalkylation: A new route toward enantioenriched pyrrolidones
Boutier, Audrey,Kammerer-Pentier, Claire,Krause, Norbert,Prestat, Guillaume,Poli, Giovanni
supporting information; experimental part, p. 3840 - 3844 (2012/06/15)
Palladium to make them, gold to cyclize them! Gold-catalyzed cycloisomerizative hydroalkylation of N-allenyl amides affords regioselectively 4-vinyl-γ-lactams. This transformation is stereospecific and takes place with a total axis-to-center chirality tra
Allene synthesis via C-C fragmentation: Method and mechanistic insight
Kolakowski, Robert V.,Manpadi, Madhuri,Zhang, Yue,Emge, Thomas J.,Williams, Lawrence J.
supporting information; experimental part, p. 12910 - 12911 (2009/12/05)
A new method of allene synthesis is described. Suitably functionalized vinyl triflates undergo fragmentation to give allenes in high yield. Computational and experimental data provide a mechanistic framework for allene formation and the complementary form
Synthesis and monoamine oxidase inhibitory activities of α-allenic amines in vivo and in vitro. Different activities of two enantiomeric allenes
Sahlberg,Ross,Fagervall,Ask,Claesson
, p. 1036 - 1042 (2007/10/02)
A series of 15 α-allenic amines, including primary, secondary, and tertiary ones, was synthesized, partly by organocopper chemistry. Their ability to inhibit mouse and rat brain mitochondrial monoamine oxidase (MAO) in vivo and in vitro, respectively, was
