21057-43-2Relevant articles and documents
Click chemistry on solid support: Synthesis of a new REM resin and application for the preparation of tertiary amines
L?ber, Stefan,Gmeiner, Peter
, p. 8699 - 8702 (2004)
1,3-Dipolar cycloaddition was employed for the synthesis of a highly practical REM resin. Exploiting this concept, the resulting triazolylmethyl acrylate (TMA) resin was used for an efficient parallel synthesis of tertiary amines by Michael addition, subs
Ruthenium-Catalyzed Chemoselective N-Allyl Cleavage: Novel Grubbs Carbene Mediated Deprotection of Allylic Amines
Alcaide, Benito,Almendros, Pedro,Alonso, Jose M.
, p. 5793 - 5799 (2007/10/03)
A novel application of the Grubbs carbene complex has been discovered. The first examples of the catalytic deprotection of allylic amines with reagents other than palladium catalysts have been achieved through Grubbs carbene mediated reaction. Significantly, the catalytic system directs the reaction toward the selective deprotection of allylic amines (secondary as well as tertiary) in the presence of allylic ethers. A variety of substrates, including enantiomerically pure multifunctional piperidines, are also usable. The new method is more convenient, chemoselective, and operationally simple than the palladium-catalyzed method. The current mechanistic hypothesis invokes a nitrogen-assisted ruthenium-catalyzed isomerization, followed by hydrolysis of the enamine intermediate. We believe that the reactive species involved in the reaction may be an Ru-H species rather than the Grubbs carbene itself. Thus, the isomerization may occur according to the hydride mechanism. The synthetic utility of this ruthenium-catalyzed allyl cleavage is illustrated by the preparation of indolizidine-type alkaloids.
Soluble polymer bound cleavage reagents: A multipolymer strategy for the cleavage of tertiary amines from REM resin
Toy, Patrick H.,Reger, Thomas S.,Janda, Kim D.
, p. 2205 - 2207 (2007/10/03)
(equation presented) Soluble polymer bound reagent 1 has been prepared to cleave tertiary amines from REM resin. Normally, amines cleaved from REM resin require extraction or chromatography to remove excess cleavage reagent and its byproducts. The solubility profile of non-crosslinked polystyrene (NCPS) based reagent 1 eliminates the need for such purification and allows for the direct isolation of a library of pure tertiary amines through simple filtration and concentration operations.