1346681-76-2Relevant academic research and scientific papers
KINETIC RESOLUTION OF CHIRAL AMINES
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Page/Page column 44; 45; 46; 47; 48; 49; 50; 51; 52, (2013/03/26)
The present invention refers to a method for the kinetic resolution of a chiral primary or secondary amine by treating the amine with a chiral, hydroxamic acid derived reagent of the formula (I). These chiral reagents are particularly useful for the kinetic resolution of cyclic amines and may be generated in situ in the presence of an N-heterocyclic carbene, thus allowing for a catalytic reaction.
Expanded substrate scope and catalyst optimization for the catalytic kinetic resolution of N-heterocycles
Hsieh, Sheng-Ying,Binanzer, Michael,Kreituss, Imants,Bode, Jeffrey W.
supporting information, p. 8892 - 8894 (2012/11/07)
The scope, reactivity, and selectivity of the chiral hydroxamic acid-catalyzed kinetic resolution of chiral amines are improved by a new catalyst structure and a more environmentally friendly reaction protocol. In addition to increasing selectivity across all substrates, these conditions make possible the resolution of N-heterocycles containing lactams or other basic functional groups that can inhibit the catalyst.
Catalytic kinetic resolution of cyclic secondary amines
Binanzer, Michael,Hsieh, Sheng-Ying,Bode, Jeffrey W.
supporting information; experimental part, p. 19698 - 19701 (2012/01/13)
The catalytic resolution of racemic cyclic amines has been achieved by an enantioselective amidation reaction featuring an achiral N-heterocyclic carbene catalyst and a new chiral hydroxamic acid cocatalyst working in concert. The reactions proceed at room temperature, do not generate nonvolatile byproducts, and provide enantioenriched amines by aqueous extraction.
