1198423-01-6Relevant articles and documents
Achieving control over the branched/linear selectivity in palladium-catalyzed allylic amination
Dubovyk, Igor,Watson, Iain D. G.,Yudin, Andrei K.
, p. 1559 - 1575 (2013/03/28)
Palladium-catalyzed reaction of unsymmetrical allylic electrophiles with amines gives rise to regioisomeric allylic amines. We have found that linear products result from the thermodynamically controlled isomerization of the initially formed branched products. The isomerization is promoted by protic acid and active palladium catalyst. The use of base shuts down the isomerization pathway and allows for the preparation and isolation of branched allylic amines. Solvent plays a key role in achieving high kinetic regioselectivity and in controlling the rate of isomerization. The isomerization can be combined with ring-closing metathesis to afford the synthesis of exocyclic allylic amines from their endocyclic precursors.
Palladium-catalyzed ring-contraction and ring-expansion reactions of cyclic allyl amines
Dubovyk, Igor,Pichugin, Dmitry,Yudin, Andrei K.
supporting information; experimental part, p. 5924 - 5926 (2011/08/04)
Ring around the rosy: An amino group can act as the leaving group or the nucleophile in a palladium-catalyzed allylic amination. As a result, readily accessible cyclic amines can be either ring contracted or ring expanded (see scheme).
Selective synthesis of eight-membered cyclic ureas by the [6 + 2] cycloaddition reaction of 2-vinylazetidines and electron-deficient isocyanates
Koya, Shunsuke,Yamanoi, Kenichi,Yamasaki, Ryu,Azumaya, Isao,Masu, Hyuma,Saito, Shinichi
supporting information; experimental part, p. 5438 - 5441 (2010/03/03)
"Chemical Equation Presented" The [6 + 2] cycloaddition reaction of 2-vinylazetidines with electron-deficient isocyanates such as tosyl isocyanate proceeded smoothly in the absence of the catalyst at room temperature, and various cyclic ureas were isolate
