65902-08-1Relevant academic research and scientific papers
Nonenzymatic kinetic resolution of amines in ionic liquids
Sabot, Cyrille,Subhash, Pithani V.,Valleix, Alain,Arseniyadis, Stellios,Mioskowski, Charles
, p. 268 - 272 (2008/09/21)
Ionic liquids are remarkably suitable and clean media for performing nonenzymatic kinetic resolution (KR) of amines through enantioselective N-acetylation: high levels of selectivity were obtained with a large variety of amines at room temperature (up to s = 30). Georg Thieme Verlag Stuttgart.
Kinetic resolution of amines: A highly enantioselective and chemoselective acetylating agent with a unique solvent-induced reversal of stereoselectivity
Arseniyadis, Stellios,Valleix, Alain,Wagner, Alain,Mioskowski, Charles
, p. 3314 - 3317 (2007/10/03)
Solvents lend a hand: Changing the polarity of the reaction solvent from 1,3-dimethyltetrahydropyrimidin-2-one (DMPU) to toluene reverses the stereo-selectivity observed in the acetylation of amines with (1S,2S)-1 (see scheme). Optimizing the reaction conditions led to an unprecedented 90% ee (S) in DMPU at -20°C with a 33% conversion.
Enzymatic resolution of bicyclic 1-heteroarylamines using Candida antarctica lipase B
Skupinska, Krystyna A.,McEachern, Ernest J.,Baird, Ian R.,Skerlj, Renato T.,Bridger, Gary J.
, p. 3546 - 3551 (2007/10/03)
Candida antarctica lipase B has been used to kinetically resolve a structurally diverse series of bicyclic 1-heteroaryl primary amines by enantioselective acetylation. High yields of either enantiomer could be obtained with excellent enantioselectivity (90-99% ee), while the undesired enantiomer could, in some cases, be recycled by thermal racemization. The absolute stereochemistry of the products was confirmed by an X-ray crystal structure.
