146407-26-3Relevant academic research and scientific papers
Carbenylative amination with N-tosylhydrazones
Khanna, Avinash,Maung, Charles,Johnson, Kyle R.,Luong, Tom T.,Van Vranken, David L.
, p. 3233 - 3235 (2012/08/08)
A Pd-catalyzed reaction of vinyl iodides and N-tosylhydrazones that assembles η3-allyl ligands through carbene insertion is demonstrated. Intramolecular trapping with nitrogen nucleophiles generates good yields of cinnamyl and pentadienyl amines like those found in alkaloid natural products. Carbenylative amination was the key reaction to complete the synthesis of the alkaloid caulophyllumine B. Migratory insertion was biased to provide allylamines with optical purity up to 64% ee, but in a lower yield.
Cyclization strategies to polyenes using Pd(II)-catalyzed couplings of pinacol vinylboronates
Iafe, Robert G.,Chan, Daniel G.,Kuo, Jonathan L.,Boon, Byron A.,Faizi, Darius J.,Saga, Tomomi,Turner, Jonathan W.,Merlic, Craig A.
, p. 4282 - 4285 (2012/10/07)
As a complement to Pd(0)-catalyzed cyclizations, seven Pd(II)-catalyzed cyclization strategies are reported. α,ω-Diynes are selectively hydroborated to bis(boronate esters), which cyclize under Pd(II)-catalysis producing a diverse array of small, medium,
Synthesis of α-CN and α-CF3 N-heterocycles through tandem nucleophilic additions
Han, Junbin,Xu, Bo,Hammond, Gerald B.
supporting information; experimental part, p. 3450 - 3453 (2011/08/07)
Using a readily available secondary aminoalkyne as starting material, a powerful strategy was discovered to prepare precursors of biologically important unnatural cyclic aminoacids and fluorinated N-heterocycles with important ring sizes (e.g., 5-7) in a
Palladium-catalysed cyclisation of N-alkynyl aminomalonates
Hess, Wilfried,Burton, Jonathan W.
supporting information; experimental part, p. 12303 - 12306 (2011/02/23)
Go around in (hetero)cycles! The palladium-catalysed tandem cyclisation/coupling reaction of alkynyl- and alkenyl-substituted aminomalonates leads to highly functionalised pyrrolidines and piperidines in good yield (see scheme). The reaction allows efficient access to a broad range of synthetically valuable building blocks.
Catalytic one-pot synthesis of cyclic amidines by virtue of tandem reactions involving intramolecular hydroamination under mild conditions
Chang, Sukbok,Lee, Minjae,Jung, Doo Young,Yoo, Eun Jeong,Cho, Seung Hwan,Han, Sun Kyu
, p. 12366 - 12367 (2007/10/03)
A new synthetic methodology for the generation of cyclic amidines has been developed by the reaction of 1,n-aminoalkynes with electron-deficient azides using a ruthenium catalyst at ambient temperature. The reaction proceeds most likely via a tandem sequence of intramolecular hydroamination of aminoalkynes, cycloaddition of azides with the resulting enamines, and rearrangement of triazoline intermediates. It demonstrates, as the proof-of-principle, that an equilibria cascade sequence can be favorably driven by an irreversible step, thus enabling a facile one-pot synthetic route to deliver molecular complexity under unprecedented mild conditions without relying on the traditional linear approaches. Copyright
