82796-68-7Relevant academic research and scientific papers
Kinetic resolution of primary amines via enantioselective N-acylation with acyl chlorides in the presence of supramolecular cyclodextrin nanocapsules
Asahara, Haruyasu,Kida, Toshiyuki,Iwamoto, Takuya,Hinoue, Tomoaki,Akashi, Mitsuru
, p. 197 - 203 (2014/01/06)
The non-enzymatic kinetic resolution of primary amines via enantioselective N-acylation with acyl chlorides was accomplished for the first time by using the selective sequestration of one enantiomer within a supramolecular cyclodextrin (CD) nanocapsule in nonpolar solvents. In addition, the first example of a crystalline structure for an inclusion complex between an acyl chloride and a CD derivative is reported.
Chiral recognition and kinetic resolution of aromatic amines via supramolecular chiral nanocapsules in nonpolar solvents
Kida, Toshiyuki,Iwamoto, Takuya,Asahara, Haruyasu,Hinoue, Tomoaki,Akashi, Mitsuru
supporting information, p. 3371 - 3374 (2013/04/24)
Herein we report the first example of chiral recognition and kinetic resolution of aromatic amine guests using supramolecular nanocapsules assembled from cyclodextrin derivatives in nonpolar media. With these nanocapsules, an extremely high chiral recognition of 1-(1-naphthyl)ethylamine (1) in cyclohexane was achieved, with a binding selectivity of up to 41 for (S)-1(R)-1. In addition, kinetic resolution of 1 through enantioselective N-acylation was accomplished with an enantiomeric excess of up to 91%.
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.
